n-decylzinc iodide | 344453-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: n-decylzinc iodide
• 英文别名: decylzinc iodide；decyl-iodo-zinc
• CAS: 344453-19-6
• 化学式: C₁₀H₂₁IZn
• 分子量: 333.571
• InChiKey: FDGUZCMQOHCDOY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  12.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  n-decylzinc iodide 、 (Z)-1-octenyl iodide 在 三(邻甲基苯基)磷 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(Z)-octadec-7-ene
  参考文献：
  名称：

  Ligand Effects on Negishi Couplings of Alkenyl Halides

  摘要：

  Negishi couplings at olefinic centers do not always occur with the anticipated maintenance of stereochemistry. The source of erosion has been traced to the ligand, and a modified method has been developed that solves the stereochemical issue and significantly improves yields of Negishi couplings in general.

  DOI：

  10.1021/ol2010165
• 作为产物：
  描述：

  1-碘癸烷 、 锌 在 1,2-二溴乙烷 、 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 10.33h， 生成 n-decylzinc iodide
  参考文献：
  名称：

  Radical Migration–Addition of N-tert-Butanesulfinyl Imines with Organozinc Reagents

  摘要：

  A novel migration-addition sequence was discovered for the reaction of enantioenriched N-tert-butanesulfinyl with iminoacetate la functionalized benzylzinc bromide reagents, producing tert-leucine derivatives in excellent diastereoselectivity (dr 98:2). The absolute configurations of two new chiral centers were unambiguously assigned by chemical transformations and X-ray crystallography. In addition, the regio- and diastereoselectivities of this novel reaction were both explained through the key N-sulfinamine intermediate M6 generated by the tert-butyl radical attack on the imine. Computational analysis of this reaction process, which was performed at the B3LYP/6-311++G(3df,2p)//B3LYP/6-31G*-LANL2DZ level, also supported our proposed two-stage mechanism.

  DOI：

  10.1021/jo401640c

文献信息

• Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overview
  作者：Martin J. Heeney、Shaya A. Al-Raqa、Aurélien Auger、Paul M. Burnham、Andrew N. Cammidge、Isabelle Chambrier、Michael J. Cook

  DOI：10.1142/s108842461330005x

  日期：2013.8

  3-dicyanohydroquinone concerned its O -alkylation to afford 3,6-dialkoxyphthalonitriles. These are immediate precursors to near-infrared absorbing phthalocyanine derivatives. Triflation of 2,3-dicyanohydroquinone extends the scope of the compound for phthalocyanine synthesis; the bis-triflate derivative is susceptible to S N Ar reactions and readily reacts with thiols to provide 3,6-bis(alkylsulfanyl) and

  本文回顾了一些合成途径，这些途径提供了 3,6-二取代酞腈，这是合成 1,4,8,11,15,18,22,25-八取代酞菁衍生物的前体。评价了使用 Diels-Alder 反应合成 3,6-二烷基、3,6-二烷氧基甲基、3,6-二烯基和 3,6-二苯基邻苯二甲腈的早期路线。然而，审查的重点集中在 2,3-二氰基氢醌作为获得 3,6-二取代邻苯二甲腈的起始原料的范围和应用。使用 2,3-二氰基氢醌的最早例子涉及其 O-烷基化以提供 3,6-二烷氧基邻苯二甲腈。这些是近红外吸收酞菁衍生物的直接前体。2,3-二氰基氢醌的三氟甲磺酸化扩展了该化合物用于合成酞菁的范围；ñAr 反应并容易与硫醇反应生成 3,6-双（烷基硫烷基）和 3,6-双（芳基硫烷基）邻苯二甲腈。3,6-双（苯基硒基）邻苯二甲腈最近也从相同的前体中获得。从中获得的酞菁衍生物通常表现出强烈的红移 Q 波段吸收，该吸收对中心金属离子特别敏感。2
• Highly Regio- and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki-Miyaura Coupling Reactions
  作者：Yasushi Nishihara、Yoshiaki Okada、Jiao Jiao、Masato Suetsugu、Ming-Tzu Lan、Megumi Kinoshita、Masayuki Iwasaki、Kentaro Takagi

  DOI：10.1002/anie.201103601

  日期：2011.9.5

  Two Nobel couplings: The synthesis of tri‐ and tetraalkylated olefins has been achieved (see scheme). These multialkylated olefins were prepared by the zirconocene‐mediated carbometalation of 1‐alkynylboronates and subsequent sequential CC bond formation with Negishi and Suzuki–Miyaura cross‐coupling reactions using β‐hydrogen‐containing alkylzinc reagents and alkyl electrophiles as coupling partners

  两种诺贝尔偶联：三和四烷基化烯烃的合成已经完成（参见方案）。这些multialkylated烯烃是由1- alkynylboronates和随后的顺序C中的茂锆-介导的carbometalation制备与根岸和铃木-宫浦C键形成交联偶合反应使用β烷基锌试剂和亲电子烷基作为偶联含α-氢的。
• Nickel-catalyzed organozinc-induced unexpected 1,3-migration of tert-butyl from sulfur to carbon in N-tert-butanesulfinyl iminoacetates
  作者：Xun Sun、Wei Zheng、Bang-Guo Wei

  DOI：10.1016/j.tetlet.2008.07.182

  日期：2008.10

  The nickel-catalyzed reaction for an unexpected 1,3-migration of tert-butyl from sulfur to carbon, upon treatment of functionalized N-tert-butanesulfinyl iminoacetate in the presence of organozinc reagent, was developed. The generality has been explored by considering the flexibility in the structure of each reactive component, organozinc halide and N-tert-butanesulfinyl iminoacetate.

  对于意外的1,3-迁移的镍-催化的反应叔丁基硫碳，处理后的官能化ñ -叔在有机锌试剂的存在-butanesulfinyl iminoacetate，被开发。一般性已探索通过考虑在每个反应性组分，有机锌卤化物和结构灵活性Ñ -叔-butanesulfinyl iminoacetate。
• Mannich‐Type Reactions of Alkylzinc Reagents
  作者：Marine Pinaud、Emilie Plantiveau、Eric Huet、Erwan Le Gall、Marc Presset

  DOI：10.1002/ejoc.202300572

  日期：2023.8.21

  The addition of alkylzinc halides to imines has been studied under different conditions. Whereas Mannich-type reactions with sulfonyl imines occurs upon simple heating, the use N-alkyl imines required an additional activation: the use of acetyl chloride led to the preparation of N-acyl tertiary amines whereas trimethylsilyl chloride afforded a direct access to unprotected secondary amines.

  在不同条件下研究了烷基卤化锌与亚胺的加成反应。虽然与磺酰亚胺的曼尼希型反应在简单加热时发生，但使用N-烷基亚胺需要额外的活化：使用乙酰氯导致制备N-酰基叔胺，而三甲基氯硅烷可直接获得未保护的仲胺。
• Highly Selective Reactions of Unbiased Alkenyl Halides and Alkylzinc Halides: Negishi-Plus Couplings
  作者：Arkady Krasovskiy、Bruce H. Lipshutz

  DOI：10.1021/ol201307y

  日期：2011.8.5

  High yielding stereo- and chemoselective Pd-catalyzed cross-couplings In THF at room temperature of alkenyl iodides and bromides with primary and secondary alkyl zinc iodides have been developed with the aid of N-methylmidazole as the key additive.