benzene | 114184-05-3

• 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
• 英文别名: {[bis(phenoxy)phosphoryloxy](hydroxy)iodo}benzene；[hydroxy((bis(phenyloxy)-phosphoryl)oxy)iodo]benzene；[Hydroxy((bis(phenyloxy)phosphoryl)oxy)-iodo]benzene；[hydroxy(phenyl)-λ3-iodanyl] diphenyl phosphate
• CAS: 114184-05-3
• 化学式: C₁₈H₁₆IO₅P
• 分子量: 470.2
• InChiKey: QUAVIMICLVDXIK-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  环丙甲基酮 、 benzene 在 水 作用下， 以 乙腈 为溶剂， 反应 2.93h， 以59%的产率得到(2-cyclopropyl-2-oxoethyl) diphenyl phosphate
  参考文献：
  名称：

  Direct .alpha.-phosphoryloxylation of ketones and (phosphoryloxy)lactonization of pentenoic acids with [hydroxy[(bis(phenyloxy)phosphoryl)oxy]iodo]benzene

  摘要：

  DOI：

  10.1021/ja00217a058
• 作为产物：
  描述：

  磷酸二苯酯 、 碘苯二乙酸 反应 0.01h， 以91%的产率得到benzene
  参考文献：
  名称：

  Rapid microwave-promoted solvent-free synthesis of hypervalent iodine reagents

  摘要：

  在微波辐照下，通过快速便捷的无溶剂配体交换反应，从（二乙酰氧基碘）炔合成了高价羟基（磺酰氧基）碘烯、羟基（磷酰氧基）碘烯和双（三氟内氧）碘苯，为在短时间内高产率合成这些高价碘试剂提供了一种简单的方法。

  DOI：

  10.3184/030823409x396427

文献信息

• Palladium-Catalyzed C–H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents
  作者：Yimiao He、Lilan Huang、Limei Xie、Peng Liu、Qiongmei Wei、Fangfang Mao、Xuehong Zhang、Jun Huang、Sijing Chen、Chusheng Huang

  DOI：10.1021/acs.joc.9b01278

  日期：2019.8.16

  simple approach for palladium-catalyzed C–H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)–H bonds, along with the hydroxylation and arylation of aryl C(sp2)–H bonds,

  开发了一种新的且操作简单的方法，该方法利用有机磷/磺酸盐高价碘试剂作为氧化剂和官能团的来源，对钯催化的CH官能化反应进行了开发。通过这种方法，在温和的条件下成功地实现了未活化的苄基C（sp 3）-H键的氧化磷酸化，磺化和羟基化，以及芳基C（sp 2）-H键的羟基化和芳基化。具有出色的站点选择性。通用的C–OSO 2 R键为随后的多样化反应提供了平台。
• Convenient, Solvent-Free Method for Preparation of [Hydroxy(phosphoryloxy)iodo]arenes
  作者：Min Zhu、Cheng Gang Cai、Wei Ke、Jing Shao

  DOI：10.1080/00397910903097229

  日期：2010.4.12

  A convenient, solvent-free method for preparation of [hydroxy(phosphoryloxy)iodo]arenes is reported. (Diacetoxyiodo)benzene or other hypervalent iodine reagents and phosphates are simply blended and ground for several minutes in an agate mortar, giving good yields of [hydroxy(phosphoryloxy)iodo]arenes with excellent purities.

  报道了一种方便的无溶剂制备 [羟基（磷酰氧基）碘] 芳烃的方法。（二乙酰氧基碘）苯或其他高价碘试剂和磷酸盐在玛瑙研钵中简单混合并研磨几分钟，得到高纯度的[羟基（磷酰氧基）碘]芳烃。
• Reactivities of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for α-Tosyloxylation and α-Phosphoryloxylation of Ketones
  作者：Takahiro Nabana、Hideo Togo

  DOI：10.1021/jo0200670

  日期：2002.6.1

  [hydroxy(tosyloxy)iodo]arenes bearing 2-thienyl, 3-thienyl, N-tosyl-4-pyrazolyl, 3-trifluoromethylphenyl, and 3,5-bis(trifluoromethy)phenyl as an aromatic group, and [hydroxy(phosphoryloxy)iodo]arenes bearing N-tosyl-4-pyrazolyl, 3-trifluoromethylphenyl, and 3,5-bis(trifluoromethy)phenyl as an aromatic group, were prepared. alpha-Tosyloxylation and alpha-phosphoryloxylation of ketones with these compounds were

  具有2-噻吩基，3-噻吩基，N-甲苯磺酰基-4-吡唑基，3-三氟甲基苯基和3,5-双（三氟甲基）苯基作为芳族基团和[羟基（磷酰氧基）的新型[羟基（甲苯磺酰氧基）碘]芳烃制备了带有N-甲苯磺酰基-4-吡唑基，3-三氟甲基苯基和3,5-双（三氟甲基）苯基作为芳香族基团的碘代芳烃。用这些化合物分别进行酮的α-甲苯磺酰化和α-磷酸酰化。将它们的反应性分别与母体[羟基（甲苯磺酰氧基）碘]苯和[羟基（磷酸甲酰氧基）碘]苯进行比较，因此将[羟基（甲苯磺酰氧基）碘]芳烃和[3]作为芳族基团的-三氟甲基苯基和3,5-双（三氟甲基）苯基显示出最佳的反应性。
• Iodophosphoryloxylation of Carbon−Carbon Multibonds and Its Application to Glycals
  作者：Takahito Muraki、Masataka Yokoyama、Hideo Togo

  DOI：10.1021/jo000296r

  日期：2000.7.1

  Iodophosphoryloxylation of carbon-carbon multibonds was attempted. Alkynes and cyclohexene were converted to the corresponding 1,2-iodophosphoryloxylated compounds in moderate to good yields with a trivalent iodine compound/iodine system, while glucal gave mainly the corresponding iodohydrin compound in this system. However, 2-deoxy-2-iodoglycosyl diphenylphosphinates were obtained from the corresponding glycals with a diphenylphosphinic acid/iodine/potassium carbonate system in good yields. Moreover, triethylborane smoothly reduced 2-deoxy-2-iodoglycosyl diphenylphosphinates to 2-deoxyglycosyl diphenylphosphinates in a 1,4-cyclohexadiene solvent.
• Regiospecific conversion of terminal alkynes to ketol phosphates with an iodine (III)-phosphate reagent
  作者：Gerald F. Koser、Xiao Chen、Kuanchiang Chen、Guoping Sun

  DOI：10.1016/0040-4039(93)89010-n

  日期：1993.1

  Terminal alkynes undergo regiospecific conversion to ketol phosphates when treated with the iodine(II)-phosphate 2 in acetonitrile containing water.