(±)-(4RS,5RS)-2-cyclohexyl-4,5-diphenyl-1,3,2-dioxaborolane | 1365543-18-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (±)-(4RS,5RS)-2-cyclohexyl-4,5-diphenyl-1,3,2-dioxaborolane
• 英文别名: (4R,5R)-C6H11B(hydrobenzoinate)
• CAS: 1365543-18-5
• 化学式: C₂₀H₂₃BO₂
• 分子量: 306.212
• InChiKey: JSIFNPWQEFTZFP-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (±)-(4RS,5RS)-2-cyclohexyl-4,5-diphenyl-1,3,2-dioxaborolane 在 双氧水 、 碘 、 magnesium 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二丁醚 、 水 为溶剂， 反应 53.0h， 生成 (±)-(4RS,5RS)-4,5-diphenyl-3-phenpropyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  On the nature of the chain-extending species in organolithium initiated stereospecific reagent-controlled homologation reactions using α-chloroalkyl aryl sulfoxides

  摘要：

  The reaction of an organolithium with an alpha-chloroalkyl aryl sulfoxide ostensibly generates an alpha-chloroalkyllithium by sulfoxide lithium exchange, but the actual identity of the chain-extending species in chlorosulfoxide-based StReCH reactions is not certain. To explore this issue, racemic 2-cyclohexyl (4R*, 5R*)-4,5-diphenyl-1,3,2-dioxaborolane was homologated by treatment with scalemic (S)-chloromethyl phenyl sulfoxide and n-BuLi (THF, -78 degrees C). The reaction proceeded without a detectable level of kinetic resolution, a finding consistent with chloromethyllithium being the active chain-extending species rather than a chiral sulfurane intermediate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.123
• 作为产物：
  描述：

  氯甲基苯亚砜 在 双氧水 、 sodium sulfate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 43.0h， 生成 (±)-(4RS,5RS)-2-cyclohexyl-4,5-diphenyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  On the nature of the chain-extending species in organolithium initiated stereospecific reagent-controlled homologation reactions using α-chloroalkyl aryl sulfoxides

  摘要：

  The reaction of an organolithium with an alpha-chloroalkyl aryl sulfoxide ostensibly generates an alpha-chloroalkyllithium by sulfoxide lithium exchange, but the actual identity of the chain-extending species in chlorosulfoxide-based StReCH reactions is not certain. To explore this issue, racemic 2-cyclohexyl (4R*, 5R*)-4,5-diphenyl-1,3,2-dioxaborolane was homologated by treatment with scalemic (S)-chloromethyl phenyl sulfoxide and n-BuLi (THF, -78 degrees C). The reaction proceeded without a detectable level of kinetic resolution, a finding consistent with chloromethyllithium being the active chain-extending species rather than a chiral sulfurane intermediate. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.123

文献信息

• Mechanism and optimisation of the homoboroproline bifunctional catalytic asymmetric aldol reaction: Lewis acid tuning through in situ esterification
  作者：Irene Georgiou、Andrew Whiting

  DOI：10.1039/c2ob06872a

  日期：——

  homoboroproline as a bifunctional catalyst in the asymmetric aldol reaction has been investigated mechanistically, particularly with respect to tuning the Lewis acidity of boron by in situ esterification with mildly sigma-electron withdrawing diols such as hydrobenzoin and tartrate esters. The stability of simple cyclohexyl and cyclopentyl boronate diol esters shows that the 5-ring boronate esters are more stable

  已通过机械方法研究了高硼脯氨酸在不对称醛醇缩合反应中作为双官能催化剂的用途，特别是通过用温和的σ电子吸取二醇（例如氢安息香和酒石酸酯）通过原位酯化来调节硼的路易斯酸度。简单的环己基和环戊基硼酸酯二醇酯的稳定性表明，五环硼酸酯更加稳定，这说明了酯化的高硼脯氨酸催化剂在烯胺介导的羟醛反应中的作用方式，这也通过NMR进行了研究。结果是优化反应以提供有效的羟醛反应和提出的机理建议。