-2-methyl-3-(phenylthio)butan-1-ol | 136057-61-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: -2-methyl-3-(phenylthio)butan-1-ol
• 英文别名: (2R,3R)-2-methyl-3-phenylsulfanylbutanol；(2R,3R)-2-methyl-3-phenylsulfanylbutan-1-ol
• CAS: 136057-61-9
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: LIIIFURZMXIECR-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  惕各酸甲酯 在 lithium aluminium tetrahydride 、 三氟甲磺酸 、 chiral amino ether-lithium thiolate 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 20.5h， 生成 -2-methyl-3-(phenylthio)butan-1-ol
  参考文献：
  名称：

  手性氨基醚控制的催化对映体选择性芳硫醇对α，β-不饱和酯和酮的加成反应：范围，结构要求和机理意义。

  摘要：

  手性氨基醚-硫醇锂络合物催化2-三甲基甲硅烷基苯硫醇与烯酸酯和烯酮的不对称共轭加成反应，并提供高对映选择性的加合物。s-顺式构象和羰基一侧的空间壁都是底物的结构要求，这些底物产生具有高对映选择性的加合物。与叔丁基烯酮的反应得到具有高对映选择性的加成产物。通过该加成-质子化序列可以构建两个连续的手性中心。钛酸甲酯被立体选择性地转化为带有两个连续手性中心的单一的95％对映体过量（ee）的合成加合物。将2-苯基-2-丁烯酸甲酯转化为单一的95％ee的加合物，然后将其脱硫为95％ee的2-苯基丁酸甲酯。

  DOI：

  10.1021/jo015879v

文献信息

• Asymmetric induction at two contiguous stereogenic centers by diastereoface differentiating nucleophilic addition reaction
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/0040-4039(91)80821-m

  日期：1991.7

  Distereoface differentiating nucleophilic of thiophenol to olefins delivers a new concomitant asymmetric construction of two contiguous stereogenic centers and has been successfully applied to the asymmetric synthesis of (+)-diltiazem.

  Distereoface区分苯酚与苯酚的亲核性，提供了一个新的伴随的两个不连续立体中心的不对称结构，并已成功地应用于（+）-地尔硫m的不对称合成。
• Asymmetric construction of two contiguous stereocenters by diastereoface differentiating addition reaction of thiols to chiral imides: Formal synthesis of (+)-diltiazem
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito

  DOI：10.1016/s0040-4020(96)01191-x

  日期：1997.2

  A high degree of diastereoselectivity has been achieved on the asymmetric construction of two contiguous stereocenters by the conjugate addition of thiols to alpha,beta-unsaturated imides possessing Evans's chiral auxiliary. Addition reactions of thiophenol to chiral E- and Z-2-methylcrotonyl imides 4 proceeded with high diastereoface selectivities. Diastereoselectivities were discussed when E- and Z-imides 4 and 5 were used as the substrates. A successful application was demonstrated by the formal synthesis of a clinically useful cardiac drug, (+)-diltiazem. (C) 1997, Elsevier Science Ltd.
• Stereospecific nucleophilic addition reactions to olefins. Addition of thiols to .alpha.,.beta.-unsaturated carboxylic acid derivatives
  作者：Okiko Miyata、Tetsuro Shinada、Ichiya Ninomiya、Takeaki Naito、Tadamasa Date、Kimio Okamura、Satoshi Inagaki

  DOI：10.1021/jo00023a021

  日期：1991.11

  Stereospecific nucleophilic addition of thiols to derivatives of alpha,beta-unsaturated carboxylic acids is described. The additions are carried out at room temperature in the presence of a catalytic amount of lithium thiolate and an excess of thiol as a proton source. Erythro and threo adducts are obtained with high diasteroselectivity from E and Z olefins, respectively. This anti addition suggests that the enolate generated by nucleophilic addition undergoes rapid protonation prior to conformational change in the intermediate.