(+)-(R)-2-methyl-1,5-heptadien-4-ol | 153254-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(R)-2-methyl-1,5-heptadien-4-ol
• 英文别名: (R)-(E)-2-Methyl-1,5-heptadien-4-ol；(E)-2-methyl-1,5-heptadien-4-ol；(4R,5E)-2-Methyl-1,5-heptadien-4-ol；(4R,5E)-2-methylhepta-1,5-dien-4-ol
• CAS: 153254-11-6
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: MDTLRZIDFDKYHS-ZJELKQJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-(R)-2-methyl-1,5-heptadien-4-ol 以70%的产率得到
  参考文献：
  名称：

  Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+, J. Org. Chem, 59 (1994) N 6, S 1444-1456

  摘要：

  DOI：
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (+)-(R)-2-methyl-1,5-heptadien-4-ol
  参考文献：
  名称：

  Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst

  摘要：

  In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.

  DOI：

  10.1021/ja00077a054

文献信息

• Oxyanion Orientation in Anionic Oxy-Cope Rearrangements
  作者：Eun Lee、Yong Rok Lee、Bongjin Moon、Ohyun Kwon、Mi Seong Shim、Jae Sook Yun

  DOI：10.1021/jo00085a037

  日期：1994.3

  Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored. It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints. Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.
• Asymmetric Synthesis of 2°- and 3°-Carbinols via <i>B</i>-Methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes
  作者：José G. Román、John A. Soderquist

  DOI：10.1021/jo701633k

  日期：2007.12.1

  [GRAPHICS]Simple Grignard procedures provide methallylboranes la and 1b in enantiomerically pure form from air-stable precursors in 98% and 95% yields, respectively. These reagents add smoothly to aldehydes and methyl ketones, respectively, providing branched 2 degrees- (6, 69-89%, 94-99% ee) and 3 degrees-(10, 71-87%, 74-96% ee) homoallylic alcohols.
• Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst
  作者：Kazuaki Ishihara、Makoto Mouri、Qingzhi Gao、Tohru Maruyama、Kyoji Furuta、Hisashi Yamamoto

  DOI：10.1021/ja00077a054

  日期：1993.12

  In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.
• Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+, J. Org. Chem, 59 (1994) N 6, S 1444-1456
  作者：Lee Eun, Lee Yong Rok, Moon Bongjin, Kwon Ohyun, Shim Mi Seong, Yun Jae S+

  DOI：——

  日期：——