(2S)-2-<(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl>-4-<(5Z)-5-(2-propynylidene)-1-cyclopenten-1-yl>-3-butyn-1,2-diol | 128878-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-<(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl>-4-<(5Z)-5-(2-propynylidene)-1-cyclopenten-1-yl>-3-butyn-1,2-diol
• 英文别名: (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(5Z)-5-prop-2-ynylidenecyclopenten-1-yl]but-3-yne-1,2-diol
• CAS: 128878-84-2
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: UXCPOWJDXHBZFN-NWKGZZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (Z)-2-[3-(Trimethylsilyl)-2-propynylidene]-cyclopentanone 在 四(三苯基膦)钯 copper(l) iodide 、 四丁基氟化铵 、 二异丁基氢化铝 、 二乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.58h， 生成 (2S)-2-<(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl>-4-<(5Z)-5-(2-propynylidene)-1-cyclopenten-1-yl>-3-butyn-1,2-diol
  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

• Synthesis and cytotoxicity of the acyclic (E)- and (Z)-dienediyne systems related to neocarzinostatine chromophore
  作者：Kazuhiko Nakatani、Katsuko Arai、Noriaki Hirayama、Fuyuhiko Matsuda、Shiro Terashima

  DOI：10.1016/0040-4039(90)80218-b

  日期：1990.1
• NAKATANI, KAZUHIKO;ARAI, KATSUKO;HIRAYAMA, NORIAKI;MATSUDA, FUYUHIKO;TERA+, TETRAHEDRON LETT., 31,(1990) N6, C. 2323-2326
  作者：NAKATANI, KAZUHIKO、ARAI, KATSUKO、HIRAYAMA, NORIAKI、MATSUDA, FUYUHIKO、TERA+

  DOI：——

  日期：——
• 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.