(3S)-7-(tert-butyldimethylsilyloxy)-1,2-epoxyirid-8-en-6-ol | 162132-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (3S)-7-(tert-butyldimethylsilyloxy)-1,2-epoxyirid-8-en-6-ol
• 英文别名: [(1S,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-prop-1-en-2-yl-6-oxabicyclo[3.1.0]hexan-1-yl]methanol
• CAS: 162132-78-7
• 化学式: C₁₆H₃₀O₃Si
• 分子量: 298.498
• InChiKey: VXFPXLPZPCRWEV-BPUTZDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-7-(tert-butyldimethylsilyloxy)-1,2-epoxyirid-8-en-6-ol 在 chromium chloride 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.5h， 生成 16-methoxy-8,9-secofusicocca-2,7,9-trien-1-ol
  参考文献：
  名称：

  Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation

  摘要：

  Starting from condensation of two iridoid synthons, (3S,8R)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene, cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction and subsequent introduction of an alpha-hydroxyl group.

  DOI：

  10.1016/s0040-4020(96)00059-2
• 作为产物：
  描述：

  (3S)-1,2-epoxyirid-8-en-6-ol 在 咪唑 、 sodium tetrahydroborate 、 Celite 、 aluminum isopropoxide 、 pyridinium chlorochromate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.0h， 生成 (3S)-7-(tert-butyldimethylsilyloxy)-1,2-epoxyirid-8-en-6-ol
  参考文献：
  名称：

  Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation

  摘要：

  Starting from condensation of two iridoid synthons, (3S,8R)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene, cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction and subsequent introduction of an alpha-hydroxyl group.

  DOI：

  10.1016/s0040-4020(96)00059-2

文献信息

• Total Synthesis of (−)-Cotylenol, a Fungal Metabolite Having a Leaf Growth Activity
  作者：Hiroaki Okamoto、Hiroaki Arita、Nobuo Kato、Hitoshi Takeshita

  DOI：10.1246/cl.1994.2335

  日期：1994.12

  Cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction followed by an oxidative formation of the 8β,9α-glycol function on the central eight-membered ring.

  Cotylenol 是一种具有 5-8-5 元三环碳骨架的代表性褐藻二萜类化合物，现在首次通过分子内烯反应形成八元环，然后氧化形成 8β,9α-中央八元环上的乙二醇功能。
• Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation
  作者：Nobuo Kato、Hiroaki Okamoto、Hitoshi Takeshita

  DOI：10.1016/s0040-4020(96)00059-2

  日期：1996.3

  Starting from condensation of two iridoid synthons, (3S,8R)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene, cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction and subsequent introduction of an alpha-hydroxyl group.