(2S)-2-(t-Butyldimethylsilyloxy)-2-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-butyn-1-ol | 140429-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-(t-Butyldimethylsilyloxy)-2-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-butyn-1-ol
• CAS: 140429-12-5
• 化学式: C₁₅H₂₈O₄Si
• 分子量: 300.47
• InChiKey: JTPQDASGHRPVCP-DOMZBBRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-(t-Butyldimethylsilyloxy)-2-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-butyn-1-ol 在 四(三苯基膦)钯 copper(l) iodide 、 pyridine-SO3 complex 、 二乙胺 、 三乙胺 作用下， 以 正己烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.09h， 生成 (2S)-2-(t-Butyldimethylsilyloxy)-2-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-4-<(5Z)-5-(3-trimethylsilyl-2-propynylidene)-1-cyclopenten-1-yl>-3-butynal
  参考文献：
  名称：

  Synthetic studies on the compounds related to neocarzinostatin chromophore. 1. Synthesis of the acyclic (E)- and (Z)-dienediyne systems

  摘要：

  The stereo-defined (E)- and (Z)-dienediyne systems related to neocarzinostatin chromophore (1) could be prepared by the coupling reaction of (E)- and (Z)-enol triflates with optically active acetylynes hearing the correct absolute stereochemistries as found in 1. Comparison of cytotoxic level of the (E)- and (Z)-dienediyne diols (32 and 33) revealed that the stereochemistry of exo-trisubstituted double bond might have a posibility to control the cytotoxicity of the acyclic analogues related to I.

  DOI：

  10.1016/s0040-4020(01)88124-2
• 作为产物：
  描述：

  (2S)-2-(t-Butyldimethylsilyloxy)-2-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-butyn-1-yl 2,2-dimethylpropanoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到(2S)-2-(t-Butyldimethylsilyloxy)-2-<(4R)-2,2-dimethyl-1,3-dioxolan-4-yl>-3-butyn-1-ol
  参考文献：
  名称：

  Synthetic studies on the compounds related to neocarzinostatin chromophore. 1. Synthesis of the acyclic (E)- and (Z)-dienediyne systems

  摘要：

  The stereo-defined (E)- and (Z)-dienediyne systems related to neocarzinostatin chromophore (1) could be prepared by the coupling reaction of (E)- and (Z)-enol triflates with optically active acetylynes hearing the correct absolute stereochemistries as found in 1. Comparison of cytotoxic level of the (E)- and (Z)-dienediyne diols (32 and 33) revealed that the stereochemistry of exo-trisubstituted double bond might have a posibility to control the cytotoxicity of the acyclic analogues related to I.

  DOI：

  10.1016/s0040-4020(01)88124-2

文献信息

• Synthetic studies on the compounds related to neocarzinostatin chromophore. 1. Synthesis of the acyclic (E)- and (Z)-dienediyne systems
  作者：Kazuhiko Nakatani、Katsuko Arai、Noriaki Hirayama、Fuyuhiko Matsuda、Shiro Terashima

  DOI：10.1016/s0040-4020(01)88124-2

  日期：——

  The stereo-defined (E)- and (Z)-dienediyne systems related to neocarzinostatin chromophore (1) could be prepared by the coupling reaction of (E)- and (Z)-enol triflates with optically active acetylynes hearing the correct absolute stereochemistries as found in 1. Comparison of cytotoxic level of the (E)- and (Z)-dienediyne diols (32 and 33) revealed that the stereochemistry of exo-trisubstituted double bond might have a posibility to control the cytotoxicity of the acyclic analogues related to I.