(R)-1-phenylundec-1-yn-3-ol

• 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)-1-phenylundec-1-yn-3-ol
• 英文别名: 1-phenyl-undec-1-yn-3-ol；(3R)-1-phenylundec-1-yn-3-ol
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: HJARSBUZMLEJSG-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  壬醛 、 苯乙炔 在 titanium(IV) isopropylate 、 2-碘代丙烷 、 (R)-5,5',6,6',7,7',8,8'-八氢-[1,1'-联萘]-2,2'-二酚 、 锌 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 40.0h， 以89%的产率得到(R)-1-phenylundec-1-yn-3-ol
  参考文献：
  名称：

  Enantioselective Alkyne Addition to Aliphatic, Aromatic, and Vinyl Aldehydes Using Zn, ⁱPrI, H₈BINOL, and Ti(OⁱPr)₄

  摘要：

  A new catalytic system based on the readily available Zn, (PrI)-Pr-i, H8BINOL, and Ti((OPr)-Pr-i)(4) has been developed which avoids the use of pyrophoric ZnEt2. It can effectively catalyze the reaction of various terminal alkynes with aromatic, aliphatic, and vinyl aldehydes to generate chiral propargylic alcohols at room temperature with up to 98% yield and 98% enantiomeric excess. This new system signifciantly expands the substrate scope of the previously reported system using Zn, EtI, BINOL, and Ti((OPr)-Pr-i)(4).

  DOI：

  10.1021/acs.joc.5b02185

文献信息

• Chiral Macrocycle-Catalyzed Highly Enantioselective Phenylacetylene Addition to Aliphatic and Vinyl Aldehydes
  作者：Zi-Bo Li、Tian-Dong Liu、Lin Pu

  DOI：10.1021/jo070091j

  日期：2007.6.1

  The 1,1‘-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of phenylacetylene to linear or branched aliphatic aldehydes and vinyl aldehydes gave various propargylic alcohols with 89−96% ee.

  发现1,1'-联萘大环（S）-2是炔烃加成醛的极佳催化剂。在室温下，在THF中存在（S）-2（20 mol％）和Me 2 Zn（2当量）的情况下，将苯乙炔添加到直链或支链脂族醛和乙烯基醛中，制得89-96％的各种炔丙醇ee。
• Highly Enantioselective Phenylacetylene Additions to Both Aliphatic and Aromatic Aldehydes
  作者：Ge Gao、David Moore、Ru-Gang Xie、Lin Pu

  DOI：10.1021/ol026921r

  日期：2002.11.1

  The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope

  发现容易获得且便宜的BINOL与Ti（O（i）Pr）（4）结合可催化炔基锌试剂与各种类型的醛反应，包括脂肪族醛，芳族醛和其他α，β-不饱和醛在室温下生成具有91-99％ee的手性炔丙醇。相对于用于该反应的醛的类型，以前的手性催化剂没有表现出如此宽的对映选择性范围。[反应：看文字]
• Synthesis of enantiopure C3-symmetric bulky trialkanolamines and their enantioselective inductivity during the alkynylation of aldehydes
  作者：An-Lin Zhang、Li-Wen Yang、Nian-Fa Yang、Jing Zhang

  DOI：10.1016/j.jorganchem.2014.10.027

  日期：2015.1

  Several C-3-symmetric trialkanolamines can be efficiently obtained via molecular sieve-assisted epoxide ring opening with ammonia in high yields (up to 90%) and regioselectivity up to 100%. These trialkanolamines were effective for the asymmetric alkynylation of aldehydes and the propargyl alcohols were obtained in high yields (up to 92%) and high enantiomeric excesses (up to 95%). The H-1 NMR spectra support that there could be a complex mixture of polynuclear Ti(IV)-based species form from the interaction of Ti(IV) with ligand. (C) 2014 Elsevier B.V. All rights reserved.