methyl 2-(((tert-butoxycarbonyl)oxy)methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate | 1138025-77-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: methyl 2-(((tert-butoxycarbonyl)oxy)methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate
• 英文别名: methyl (1R,2S,6S)-2-[(2-methylpropan-2-yl)oxycarbonyloxymethyl]-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate
• CAS: 1138025-77-0
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: VCVOCVHOUVYQHY-BHDSKKPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(((tert-butoxycarbonyl)oxy)methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate 在 高氯酸 、 水 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Stereocontrolled total synthesis of (−)-myriocin

  摘要：

  The stereocontrolled total synthesis of (-)-myriocin 1 is reported. Optically active epoxide 9 was converted from symmetrical cyclohexadiene 8, utilizing an enzymatic kinetic resolution. The three sequential stereogenic centers of 1 were constructed by a regioselective epoxide-opening reaction and a Hofmann rearrangement. Elongation of the side chain was efficiently accomplished by the Julia-Kocienski reaction. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.12.020
• 作为产物：
  描述：

  (1S,2R,6R)-methyl 2-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 methyl 2-(((tert-butoxycarbonyl)oxy)methyl)-7-oxabicyclo[4.1.0]hept-3-ene-2-carboxylate
  参考文献：
  名称：

  Catalytic Desymmetrization of Cyclohexadienes by Asymmetric Bromolactonization

  摘要：

  Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.

  DOI：

  10.1021/ol302908a