(10R)-B-[(Z)-γ-methoxyallyl]-10-trimethylsilyl-9-borabicyclo[3.3.2]decane | 1161746-10-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (10R)-B-[(Z)-γ-methoxyallyl]-10-trimethylsilyl-9-borabicyclo[3.3.2]decane
• 英文别名: (10R)-B-[(Z)-(γ-methoxyallyl)]-10-TMS-9-BBD；[(10R)-9-[(Z)-3-methoxyprop-2-enyl]-9-borabicyclo[3.3.2]decan-10-yl]-trimethylsilane
• CAS: 1161746-10-6
• 化学式: C₁₆H₃₁BOSi
• 分子量: 278.318
• InChiKey: JKIBMOPKPPSEEP-USIKEBEKSA-N

物化性质

• 沸点：
  343.9±42.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (E)-(cyclohexylmethyleneamino)-diisobutylaluminum 、 (10R)-B-[(Z)-γ-methoxyallyl]-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes

  摘要：

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.

  DOI：

  10.1021/ol900865y
• 作为产物：
  描述：

  (-)-(10R)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 、 烯丙基甲基醚 在 仲丁基锂 、 三甲基氯硅烷 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 3.0h， 以85%的产率得到(10R)-B-[(Z)-γ-methoxyallyl]-10-trimethylsilyl-9-borabicyclo[3.3.2]decane
  参考文献：
  名称：

  Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes

  摘要：

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.

  DOI：

  10.1021/ol900865y

文献信息

• Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes
  作者：Lorell Muñoz-Hernández、John A. Soderquist

  DOI：10.1021/ol900865y

  日期：2009.6.18

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.