(-)-(3R)-3-methylhex-5-ene-3-ol | 100334-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(3R)-3-methylhex-5-ene-3-ol
• 英文别名: (R)-3-methyl-hex-5-en-3-ol；4-Methyl-1-hexen-4-ol；(3R)-3-methylhex-5-en-3-ol
• CAS: 100334-48-3
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: GBARKLJMQRUBKV-SSDOTTSWSA-N

物化性质

• 沸点：
  85 °C(Press: 90 Torr)
• 密度：
  0.835±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 氨 、 sodium 作用下， 生成 (-)-(3R)-3-methylhex-5-ene-3-ol 、 (+)-(3S)-3-methylhex-5-ene-3-ol
  参考文献：
  名称：

  Enantioselective Synthesis of Tertiary Homoallylic Alcohols via Diastereoselective Addition of Allylsilanes to Ketones

  摘要：

  DOI：

  10.1021/ja00126a025

文献信息

• <i>B</i>-Allyl-10-Ph-9-borabicyclo[3.3.2]decanes:  Strategically Designed for the Asymmetric Allylboration of Ketones
  作者：Eda Canales、K. Ganeshwar Prasad、John A. Soderquist

  DOI：10.1021/ja053865r

  日期：2005.8.24

  bicyclic structure. In addition to providing the homoallylic alcohols 6 efficiently (70-92%), the procedure also permits the efficient recovery of the chiral boron moiety (67-82%) as an air-stable crystalline N-methylpseudoephedrine complex 4 for the direct regeneration of 1 with allylmagnesium bromide in ether (98%). The reagent gives predictable stereochemistry, providing a strategically designed "chiral

  报道了两种对映体形式的 B-烯丙基-10-(苯基)-9-硼双环 [3.3.2] 癸烷 (1) 的简单有效合成。当该过程在 0 摄氏度进行时，这些试剂在 -78 摄氏度烯丙基硼化过程中的显着对映选择性 (81-99% ee) 仅适度减弱，这种现象归因于其刚性双环结构。除了有效地提供高烯丙醇 6 (70-92%)，该程序还允许有效回收手性硼部分 (67-82%) 作为空气稳定的结晶 N-甲基伪麻黄碱复合物 4，用于直接再生1 与乙醚中的烯丙基溴化镁 (98%)。该试剂提供可预测的立体化学，提供一个战略性设计的“手性口袋”，特别容易接受领先的甲基（例如，
• Synthesis of Enantiopure Homoallylic Alcohols
  作者：Lutz F. Tietze、Kai Schiemann、Christoph Wegner、Christian Wulff

  DOI：10.1002/(sici)1521-3765(19980904)4:9<1862::aid-chem1862>3.0.co;2-c

  日期：1998.9.4

  A highly selective asymmetric domino allylation of aliphatic ketones is described. When methyl ketones 1a-g, the chiral trimethylsilyl ether 2, and allylsilane 3 react in the presence of catalytic amounts of trifluoromethanesulfonic acid, the homoallylic ethers 4a-g are produced with up to 24:1 diastereoselectivity and 89% yield. Cleavage of the obtained tertiary homoallylic ethers C using lithium or sodium in liquid ammonia gives the homoallytic alcohols 5 in 75 to 95% yield and up to 92% ee. Even ethyl methyl ketone 1a, the most difficult example, showed a stereoselectivity of 9:1 at -78 degrees C and 24:1 at -109 degrees C. In addition, the allylation of protected hydroxyalkyl methyl ketones 7a-j was investigated to give the corresponding homoallylic ethers 8a-j with a diastereoselectivity of up to >24:1 and 98% yield. In contrast, ethyl alkyl ketones 1h-j have a low selectivity.
• JADHAV, P. K.;BHAT, K. S.;PERUMAL, P. T.;BROWN, H. C., J. ORG. CHEM., 1986, 51, N 4, 432-439
  作者：JADHAV, P. K.、BHAT, K. S.、PERUMAL, P. T.、BROWN, H. C.

  DOI：——

  日期：——
• COPPI L.; MORDINI A.; TADDEI M., TETRAHEDRON LETT., 28,(1987) N 9, 969-972
  作者：COPPI L.、 MORDINI A.、 TADDEI M.

  DOI：——

  日期：——
• Enantioselective Synthesis of Tertiary Homoallylic Alcohols via Diastereoselective Addition of Allylsilanes to Ketones
  作者：Lutz F. Tietze、Kai Schiemann、Christoph Wegner

  DOI：10.1021/ja00126a025

  日期：1995.5