benzene,iodozinc(1+) | 23665-09-0

• 物质功能分类: 有机原料 - 有机金属类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzene,iodozinc(1+)
• 英文别名: phenylzinc iodide；phenylzinc(II) iodide
• CAS: 23665-09-0
• 化学式: C₆H₅IZn
• 分子量: 269.4
• InChiKey: NTIQTKXSDRUAOC-UHFFFAOYSA-M

物化性质

• 密度：
  0.966 g/mL at 25 °C
• 闪点：
  1 °F
• 暴露限值：
  ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)OSHA: TWA 200 ppm(590 mg/m3)NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

安全信息

• 危险等级：
  4.3
• 危险品标志：
  F,C
• 安全说明：
  S16,S26,S36/37/39,S45
• 危险类别码：
  R34,R14/15,R19,R11
• 海关编码：
  2931900090
• WGK Germany：
  3
• 危险标志：
  GHS02,GHS07,GHS08
• 危险品运输编号：
  UN 3399 4.3/PG 2
• 危险性描述：
  H225,H261,H302,H315,H319,H335,H351
• 危险性防范说明：
  P210,P231 + P232,P280,P370 + P378,P402 + P404,P403 + P235

反应信息

• 作为反应物：
  描述：

  benzene,iodozinc(1+) 在 四(三苯基膦)钯 N-氯代丁二酰亚胺 作用下， 以 乙二醇二甲醚 为溶剂， 以95%的产率得到联苯
  参考文献：
  名称：

  Palladium-Catalyzed Synthesis of Biaryls from Arylzinc Compounds UsingN-Chlorosuccinimide or Oxygen as an Oxidant

  摘要：

  在少量 Pd2+ 或 Pd0 催化剂存在下，使用 N-氯代琥珀酰亚胺(NCS)或氧气作为氧化剂，实现了芳基锌化合物的氧化自偶联。根据氧化剂的不同，催化反应涉及不同的反应途径；NCS 或氧气可能分别将 I- 或 Pd0 氧化成 I+ 或 Pd2+。这个反应通过芳基锌中间体，提供了一种从芳基卤化物或芳烃合成联芳基化合物的新型简便方法。

  DOI：

  10.1246/bcsj.74.2415
• 作为产物：
  描述：

  锌 在 碘苯 作用下， 以 further solvent(s) 为溶剂， 生成 benzene,iodozinc(1+)
  参考文献：
  名称：

  Ultrasound-Promoted Synthesis of Arylzinc Compounds Using Zinc Powder and Their Application to Palladium(0)-Catalyzed Synthesis of Multifunctional Biaryls

  摘要：

  含有电子吸引基团（如 CO2CH3、CON(CH3)2、CN、Br、Cl 或 CF3）在邻位的芳基锌化合物，通过超声促进的芳基碘化物与锌粉的反应容易制备，随后用于钯(0)催化的交叉偶联反应，与芳基卤化物反应，得到不对称且多功能的双芳基化合物，产率良好。

  DOI：

  10.1246/cl.1993.469
• 作为试剂：
  描述：

  碘苯 、 碘甲基膦酸二乙酯 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,1'-bis(diphenylphosphino)ferrocene 、 benzene,iodozinc(1+) 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以80%的产率得到苯基膦酸二乙酯
  参考文献：
  名称：

  Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted Alkylarenes

  摘要：

  The catalytic cross-coupling between ArZnX and ICH2(CH2)(n)P(O)(OEt)(2) (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, P-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.

  DOI：

  10.1021/jo900142b

文献信息

• Copper-Catalyzed Electrophilic Amination of Diorganozinc Reagents
  作者：Ashley M. Berman、Jeffrey S. Johnson

  DOI：10.1021/ja049474e

  日期：2004.5.1

  The copper-catalyzed electrophilic amination of diorganozinc reagents employing O-acyl N,N-dialkyl hydroxylamine derivatives as aminating agents is described. This reaction offers a general method for the preparation of tertiary amines in high yields and is noteworthy for its convenience both in terms of reaction conditions employed (room temperature,

  描述了使用 O-酰基 N,N-二烷基羟胺衍生物作为胺化剂的二有机锌试剂的铜催化亲电胺化。该反应提供了一种以高产率制备叔胺的通用方法，并且在所采用的反应条件（室温、
• Nickel‐Catalyzed α‐Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ‐Diarylcarbonyl and Aryltetralone Derivatives
  作者：Shekhar KC、Roshan K. Dhungana、Namrata Khanal、Ramesh Giri

  DOI：10.1002/anie.201913435

  日期：2020.5.18

  We report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary and tertiary α-halocarbonyl molecules, and electronically varied arylzinc reagents. The reaction generates γ,γ-diarylcarbonyl derivatives with α-secondary, tertiary and quaternary carbon centers. The products can be readily converted

  我们报告了镍催化的乙烯基芳烃与α-卤代羰基化合物和芳基锌试剂的镍催化区域选择性α-羰基烷基芳基化。该反应适用于伯，仲和叔α-卤代羰基分子，以及电子化的芳基锌试剂。该反应产生具有α-仲，叔和季碳中心的γ，γ-二芳基羰基衍生物。该产品可以轻松转化为芳基四氢萘酮，包括抗抑郁药Zoloft的前体。
• Palladium-Catalyzed Cross-Coupling Reactions of Carboxylic Anhydrides with Organozinc Reagents
  作者：Donghui Wang、Zhaoguo Zhang

  DOI：10.1021/ol035801w

  日期：2003.11.1

  [reaction: see text] Negishi-type cross-coupling reaction was effected by employing organozincs and anhydrides or mixed anhydrides that formed in situ from sodium salts of the corresponding acids and ethyl chloroformate under the catalysis of palladium(0). A general method for preparing symmetrical/unsymmetrical ketones was developed.

  [反应：见正文] Negishi型交叉偶联反应是通过使用有机锌和酸酐或混合酸酐（由相应酸的钠盐和氯甲酸乙酯在钯（0）催化下原位形成）而进行的。开发了一种制备对称/不对称酮的通用方法。
• Stereoconvergent Arylations and Alkenylations of Unactivated Alkyl Electrophiles: Catalytic Enantioselective Synthesis of Secondary Sulfonamides and Sulfones
  作者：Junwon Choi、Pablo Martín-Gago、Gregory C. Fu

  DOI：10.1021/ja506885s

  日期：2014.8.27

  controlling the stereochemistry of the sulfur-bearing carbon of such targets. In this report, we describe nickel-catalyzed stereoconvergent Negishi arylations and alkenylations of racemic α-bromosulfonamides and -sulfones that furnish the desired cross-coupling product in very good ee and yield for an array of reaction partners. Mechanistic studies are consistent with the generation of a radical intermediate

  开发用于生成对映体富集的磺酰胺和砜的有效方法是有机合成和药物化学等领域的重要目标；然而，关于直接催化不对称方法来控制此类目标的含硫碳的立体化学的报道相对较少。在本报告中，我们描述了镍催化的立体收敛 Negishi 芳基化和外消旋 α-溴磺酰胺和 - 砜的烯基化，它们以非常好的 ee 和产率为一系列反应伙伴提供所需的交叉偶联产物。机理研究与自由基中间体的产生一致，该中间体具有足够的寿命以扩散出溶剂笼并环化到侧链烯烃上。
• [EN] ANALOGS OF DISCODERMOLIDE AND DICTYOSTATIN-1, INTERMEDIATES THEREFOR AND METHODS OF SYNTHESIS THEREOF<br/>[FR] ANALOGUES DE DISCODERMOLIDE ET DE DICTYOSTATINE-1, INTERMEDIAIRES CORRESPONDANTS, ET PROCEDES DE SYNTHESE CORRESPONDANTS
  申请人：UNIV PITTSBURGH

  公开号：WO2004022552A1

  公开（公告）日：2004-03-18

  A compound of the following structure: wherein R1 is H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; R2 is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; Ra, Rb and Rc are independently an alkyl group or an aryl group; Rd is an alkyl group, an aryl group, an alkoxylalkyl group, -RiSiRaRbRc or a benzyl group, wherein Ri is an alkylene group; Re is an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or -NRgRh, wherein Rg and Rh are independently H, an alkyl group or an aryl group; R3 is (CH2)n where n is and integer in the range of 0 to 5, -CH2CH(CH3)-, -CH=CH-, -CH=C(CH3)-, or -C=-C-; R4 is (CH2)p where p is an integer in the range of 4 to 12, -(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs I)CH(Rs2)C(Rs3)=C(Rs4)-, -(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-, -(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-, wherein y1 and y2 are 1 and y3, y4 and y5 are independently 0 or 1, Rk1, Rk2, Rk3, Rk4 and Rk5 are independently H, CH3, or OR2a, and Rs1, Rs2, Rs3, and Rs4 are independently H or CH3, wherein R2a is H, an alkyl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; and R5 is H or OR2b, wherein R2b is H, an alkyl group, an aryl group, an aryl group, a benzyl group, a trityl group, -SiRaRbRc, CH2ORd, or CORe; provided that the compound is not dictyostatin 1.

  以下是该结构的化合物：其中R1为H、烷基基团、芳基、烯基基团、炔基基团或卤素原子；R2为H、烷基基团、芳基、苄基、三苄基、-SiRaRbRc、 ORd或CORe；Ra、Rb和Rc独立地为烷基基团或芳基；Rd为烷基基团、芳基、烷氧基烷基团、-RiSiRaRbRc或苄基，其中Ri为烷基烷基团；Re为烷基基团、烯丙基基团、苄基、芳基、烷氧基或-NRgRh，其中Rg和Rh独立地为H、烷基基团或芳基；R3为(CH2)n，其中n为0到5范围内的整数，- CH(CH3)-、-CH=CH-、-CH=C( )-或-C=-C-；R4为( )p，其中p为4到12范围内的整数，-(CHRkl)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5C(Rsl )=C(Rs2)C(Rs3)=C(Rs4)-、-(CHRk1 )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rs I)CH(Rs2)C(Rs3)=C(Rs4)-、-(CHRk1)yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRks)y5C(Rsl)=C(Rs2)CH(Rs3)CH(Rs4)-、-(CHRkI )yl (CHRk2)y2(CHRk3)y3(CHRk4)y4(CHRk5)y5CH(Rsl)CH(Rs2)CH(Rs3)CH(R s4)-，其中y1和y2为1，y3、y4和y5独立地为0或1，Rk1、Rk2、Rk3、Rk4和Rk5独立地为H、 或OR2a，Rs1、Rs2、Rs3和Rs4独立地为H或 ，其中R2a为H、烷基基团、芳基、苄基、三苄基、-SiRaRbRc、 ORd或CORe；R5为H或OR2b，其中R2b为H、烷基基团、芳基、芳基、苄基、三苄基、-SiRaRbRc、 ORd或CORe；前提是该化合物不是dictyostatin 1。