2-Benzylsulfanyl-butane-1,4-diol | 68381-60-2

• 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: 2-Benzylsulfanyl-butane-1,4-diol
• 英文别名: 2-Benzylsulfanylbutane-1,4-diol；2-benzylsulfanylbutane-1,4-diol
• CAS: 68381-60-2
• 化学式: C₁₁H₁₆O₂S
• 分子量: 212.313
• InChiKey: ARBIBLCCQANWLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Benzylsulfanyl-butane-1,4-diol 在 吡啶 、 双氧水 、 ortho-tungstic acid 作用下， 生成 Methanesulfonic acid 4-methanesulfonyloxy-2-phenylmethanesulfonyl-butyl ester
  参考文献：
  名称：

  Potential bis-alkylating agents for cancer chemotherapy. Approaches to the synthesis of 2-sulfonyl-1,4-bis(dimethanesulfonoxy)butanes

  摘要：

  Three general methods for the synthesis of derivatives of the bis-alkylating agent, myleran [1,4-bis(methane-sulfonoxy)butane (1)], are presented. These derivatives contain a lipophilic group attached to the 2 position of 1,4-bis(methanesulfonoxy)butane by means of a sulfonyl function. As examples of the scope of the methods, the synthesis of seven such derivatives (12a-g) is presented. All seven were inactive against L1210 and P388 leukemia in the mouse.

  DOI：

  10.1021/jm00209a017
• 作为产物：
  描述：

  Benzylmercapto-bernsteinsaeurediethylester 在 lithium aluminium tetrahydride 作用下， 生成 2-Benzylsulfanyl-butane-1,4-diol
  参考文献：
  名称：

  Potential bis-alkylating agents for cancer chemotherapy. Approaches to the synthesis of 2-sulfonyl-1,4-bis(dimethanesulfonoxy)butanes

  摘要：

  Three general methods for the synthesis of derivatives of the bis-alkylating agent, myleran [1,4-bis(methane-sulfonoxy)butane (1)], are presented. These derivatives contain a lipophilic group attached to the 2 position of 1,4-bis(methanesulfonoxy)butane by means of a sulfonyl function. As examples of the scope of the methods, the synthesis of seven such derivatives (12a-g) is presented. All seven were inactive against L1210 and P388 leukemia in the mouse.

  DOI：

  10.1021/jm00209a017

文献信息

• Lipase Catalyzed Regioselective Esterification of a Terminal Diol
  作者：Claudio Fuganti、Giuseppe Pedrocchi-Fantoni、Stefano Servi

  DOI：10.1246/cl.1990.1137

  日期：1990.7

  Lipase from Candida cylindracea catalyzes regioselective interesterification between an acyl donor and a terminal diol. Discrimination between primary hydroxyl groups in a dissymmetric molecule has not been previously described. Preparation of (R)-2-thiobenzyl-4-acetoxy-hydroxybutane 4 obtained in this way, allows the assignement of the (R) absolute configuration to 2-thiobenzyl-1,4-butandiol derivatives previously obtained in a yeast transformation.

  圆筒状念珠菌的脂肪酶催化酰基供体和末端二醇之间的区域选择性酯交换反应。不对称分子中伯羟基之间的区别此前尚未被描述。通过这种方法获得的（R）-2-硫代苄基-4-乙酰氧基-羟基丁烷4的制备，使得先前通过酵母转化获得的2-硫代苄基-1,4-丁二醇衍生物的（R）绝对构型得以确定。