<(Z)-γ-methoxyallyl>diisocampheylborane | 112482-55-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: <(Z)-γ-methoxyallyl>diisocampheylborane
• 英文别名: {(Z)-γ-methoxyallyl}diisopinocampheylborane；((Z)-γ-methoxyallyl)diisocampheylborane；[(Z)-3-methoxyprop-2-enyl]-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane
• CAS: 112482-55-0；116376-27-3；112571-25-2
• 化学式: C₂₄H₄₁BO
• 分子量: 356.4
• InChiKey: REIADFKXVYZJJI-GFGOAYLJSA-N

物化性质

• 沸点：
  420.9±34.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  <(Z)-γ-methoxyallyl>diisocampheylborane 、 (E,4S,5R,6S,8S,9R)-9-(2,5-dimethoxy-3-nitrophenyl)-5,6,9-trimethoxy-2,4,8-trimethylnon-2-enal 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以77%的产率得到12-(2,5-dimethoxy-3-nitro-phenyl)-3,8,9,12-tetramethoxy-5,7,11-trimethyl-dodeca-1,5-diene-4-ol
  参考文献：
  名称：

  Total Synthesis of Herbimycin A

  摘要：

  Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's a-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.

  DOI：

  10.1021/ol036092p
• 作为产物：
  描述：

  在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 生成 <(Z)-γ-methoxyallyl>diisocampheylborane
  参考文献：
  名称：

  Chiral synthesis via organoboranes. 13. A highly diastereoselective and enantioselective addition of [(Z)-.gamma.-alkoxyallyl]diisopinocampheylboranes to aldehydes

  摘要：

  DOI：

  10.1021/ja00213a029

文献信息

• Heteroatom-directed Wacker oxidations. A protection-free synthesis of (−)-heliophenanthrone
  作者：Parag Mukherjee、Tarun K. Sarkar

  DOI：10.1039/c2ob07095b

  日期：——

  of (−)-heliophenanthrone has been achieved without any protection–deprotection protocol at an overall yield of 28%. Key features of this synthesis comprise a heteroatom-directed Wacker oxidation of an internal cyclic olefin in addition to asymmetric Brown allylation and ring closing metathesis (RCM).

  第一对映体的六步合成 （-）-螺菲蒽酮无需任何保护-脱保护方案即可实现，总收率为28％。该合成的关键特征包括除不对称布朗烯丙基化和闭环复分解（RCM）之外，内部环烯烃的杂原子定向瓦克氧化。
• Diastereoselective synthesis of unsaturated 1,2-amino alcohols from α-hydroxy allyl ethers using chlorosulfonyl isocyanate
  作者：Ji Duck Kim、In Soo Kim、Jin Cheng Hua、Ok Pyo Zee、Young Hoon Jung

  DOI：10.1016/j.tetlet.2004.12.100

  日期：2005.2

  Diastereoselective synthesis of 1,2-amino alcohols was achieved from a highly diastereoselective allylic amination reaction of α-hydroxy allyl ethers using chlorosulfonyl isocyanate. Diastereoselectivities varied depending on the stereochemistry of the ethers used and the stability of the carbocation intermediate obtained during the reaction. We propose that this CSI reaction is the results of either

  使用氯磺酰基异氰酸酯通过α-羟基烯丙基醚的高度非对映选择性烯丙基胺化反应可实现1,2-氨基醇的非对映选择性合成。非对映选择性根据所用醚的立体化学和反应过程中获得的碳阳离子中间体的稳定性而变化。我们建议，根据碳阳离子中间体的稳定性，该CSI反应是S N i或S N 1机制的结果。
• Total Synthesis of Herbimycin A
  作者：Sophie Canova、Véronique Bellosta、Antony Bigot、Patrick Mailliet、Serge Mignani、Janine Cossy

  DOI：10.1021/ol062642i

  日期：2007.1.1

  Hsp90 has recently emerged as a promising biological target for treatment of cancer. Herbimycin A and other members of the benzoquinoid ansamycin class of natural products are known to inhibit Hsp90 activity. The total synthesis of herbimycin A was achieved from the commercially available Roche ester 1 by using allylmetals to control the stereogenic centers at C6, C7, C10, C11, and C12 and a ring-closing metathesis to control the (Z)-double bond of the (E,Z)-dienic moiety.
• Chiral synthesis via organoboranes. 13. A highly diastereoselective and enantioselective addition of [(Z)-.gamma.-alkoxyallyl]diisopinocampheylboranes to aldehydes
  作者：Herbert C. Brown、Prabhakar K. Jadhav、Krishna S. Bhat

  DOI：10.1021/ja00213a029

  日期：1988.3