(R)-(E)-2,2-dimethyl-4-undecen-3-ol | 857678-59-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(E)-2,2-dimethyl-4-undecen-3-ol
• 英文别名: 2,2-dimethyl-undec-4-en-3-ol；(E,3R)-2,2-dimethylundec-4-en-3-ol
• CAS: 857678-59-2
• 化学式: C₁₃H₂₆O
• 分子量: 198.349
• InChiKey: GLCCNDGEHUGTRE-HCRIHEDKSA-N

物化性质

• 沸点：
  242.0±8.0 °C(Predicted)
• 密度：
  0.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  1-辛炔 在 diethylzinc 作用下， 以 正己烷 为溶剂， 反应 15.0h， 生成 (R)-(E)-2,2-dimethyl-4-undecen-3-ol
  参考文献：
  名称：

  [2,2]Paracyclophane-Based N,O-Ligands in Alkenylzinc Additions to Aldehydes

  摘要：

  [GRAPHICS]The application of planar and central chiral [2,2]paracyclophane-based N,O-ligands in asymmetric alkenylzinc additions to various aldehydes is described, which gives rise to very high ee's especially for difficult substrates. A fine-tuning of the alkenylzinc species by employing different transmetalation reagents is reported, allowing control of the steric bulk of the alkenylzinc species and thus the selectivity of the catalysis.

  DOI：

  10.1021/ol016954r

文献信息

• Catalytic asymmetric synthesis ofSecondary (E)-allyl alcohols from acetylenes and aldehydesvia (1-alkenyl)zinc intermediates. Preliminary Communication
  作者：Wolfgang Oppolzer、Rumen N. Radinov

  DOI：10.1002/hlca.19920750114

  日期：1992.2.5

  mol-equiv., hexane), treatment of the resulting [(E)-1-alkenyl]boranes 5 with Et2Zn or Me2Zn (1.05 mol-equiv.) followed by addition of (−)-3-exo-(dimethylamino)isoborneol (DAIB, 8; 0.01 mol-equiv.), subsequent addition of a solution of an aromatic or aliphatic aldehyde (1 mol-equiv., hexane), and quenching with aq. NH4Cl provided (E)-allyl alcohols 6 usually in 70–95% yield with 79–98% enantiomeric

  用新鲜制备的二环己基硼烷（1摩尔当量，己烷）对脂肪族1-炔烃进行硼氢化，用Et 2 Zn或Me 2 Zn（1.05摩尔当量）处理所得的[（E）-1-烯基]硼烷5。然后加入（-）-3-外-（二甲基氨基）异冰片醇（DAIB，8 ; 0.01摩尔当量），随后加入芳香或脂族醛溶液（1摩尔当量，己烷），和用水溶液淬灭。NH 4 Cl提供的（E）-烯丙基醇6的收率通常为70-95％，对映体过量为79-98％（方案3和表）。
• Asymmetric Hydrogenation of <i>tert</i>-Alkyl Ketones
  作者：Takeshi Ohkuma、Christian A. Sandoval、Rajagopal Srinivasan、Quinghong Lin、Yinmao Wei、Kilian Muñiz、Ryoji Noyori

  DOI：10.1021/ja052071+

  日期：2005.6.1

  A combined system of RuCl2(tolbinap)(pica) and an alkaline or organic phosphazene base catalyzes asymmetric hydrogenation of sterically congested tert-alkyl ketones (TolBINAP = 2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl, PICA = alpha-picolylamine). Hydrogenation with RuH(eta1-BH4)(tolbinap)(pica) does not require any strong base. Alcoholic solvents strongly affect the catalytic efficiency. The reaction proceeds smoothly in ethanol under 1-20 atm of H2 and at room temperature with a substrate to catalyst molar ratio of up to 100 000. Various aliphatic, aromatic, heteroaromatic, and olefinic tert-alkyl ketones are convertible to the corresponding chiral carbinols in high enantiomeric purity. Olefinic and heteroaromatic functions are left intact. Certain cyclic ketones are also usable. The mode of enantioface selection is consistent and predictable.
• [2,2]Paracyclophane-Based <i>N</i>,<i>O</i>-Ligands in Alkenylzinc Additions to Aldehydes
  作者：Stefan Dahmen、Stefan Bräse

  DOI：10.1021/ol016954r

  日期：2001.12.1

  [GRAPHICS]The application of planar and central chiral [2,2]paracyclophane-based N,O-ligands in asymmetric alkenylzinc additions to various aldehydes is described, which gives rise to very high ee's especially for difficult substrates. A fine-tuning of the alkenylzinc species by employing different transmetalation reagents is reported, allowing control of the steric bulk of the alkenylzinc species and thus the selectivity of the catalysis.