(E)-7-phenyl-6-hepten-1-ol | 117324-65-9

• 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: (E)-7-phenyl-6-hepten-1-ol
• 英文别名: (E)-7-phenylhept-6-en-1-ol
• CAS: 117324-65-9
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: YXIALDUVLSSVFS-WEVVVXLNSA-N

物化性质

• 沸点：
  322.2±21.0 °C(Predicted)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 在 正丁基锂 、 草酰氯 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 45.5h， 生成 (E)-7-phenyl-6-hepten-1-ol
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation

  摘要：

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.

  DOI：

  10.1021/ja00019a038

文献信息

• Dinuclear Cobalt Complex-Catalyzed Stereodivergent Semireduction of Alkynes: Switchable Selectivities Controlled by H₂O
  作者：Ke Chen、Hongdan Zhu、Yuling Li、Qian Peng、Yinlong Guo、Xiaoming Wang

  DOI：10.1021/acscatal.1c04141

  日期：2021.11.5

  Catalytic semireduction of internal alkynes to alkenes is very important for organic synthesis. Although great success has been achieved in this area, switchable Z/E stereoselectivity based on a single catalyst for the semireduction of internal alkynes is a longstanding challenge due to the multi-chemo- and stereoselectivity, especially based on less-expensive earth-abundant metals. Herein, we describe

  内部炔烃催化半还原成烯烃对于有机合成非常重要。尽管在该领域取得了巨大成功，但由于多化学和立体选择性，特别是基于较便宜的地球丰富金属，基于单一催化剂的可切换Z / E立体选择性是一个长期的挑战，用于内部炔烃的半还原. 在此，我们描述了由大环双吡啶基二亚胺 (PDI) 配体支持的双核钴络合物催化的炔烃到 ( Z )- 或 ( E )-烯烃的可切换半还原。发现炔烃的顺式还原首先发生，Z - E烯烃stereoisomerization过程正式由H的量来控制2 O，因为H的浓度2 O可能会影响催化剂异构化的催化活性。因此，该协议提供了一种通过调整水量在单个转化中转换为 ( Z )- 或 ( E )-烯烃异构体的简便方法。
• PROCESS FOR PRODUCING POLYMER WITH FUNCTIONAL END
  申请人：KURARAY CO., LTD.

  公开号：EP1721912A1

  公开（公告）日：2006-11-15

  An organolithium compound represented by the following general formula (i): (i) [wherein A represents a heteroatom selected among oxygen, nitrogen, sulfur, and phosphorus; Ar represents optionally substituted aryl; R1 represents C1-10 alkyl; R2 represents C1-10 alkylene; R3 represents C1-10 alkyl or a protective group for the functional group -A-H (A is a heteroatom); and when the heteroatom A is oxygen or sulfur, then m and n each is 0 or 1, provided that the sum of m and n is 1, and when the heteroatom A is nitrogen or phosphorus, then m and n each is 0, 1, or 2, provided that the sum of m and n is 2], which has not hitherto been used in anionic polymerization, is used as an anionic polymerization initiator to easily and smoothly produce a polymer having a functional group at an end.

  由以下通式(i)代表的有机锂化合物：(i) [其中 A 代表选自氧、氮、硫和磷的杂原子；Ar 代表任选取代的芳基；R1 代表 C1-10 烷基；R2 代表 C1-10 亚烷基；R3 代表 C1-10 烷基或官能团 -A-H 的保护基（A 为杂原子）；当杂原子 A 为氧或硫时，则 m 和 n 各为 0 或 1，条件是 m 和 n 之和为 1；当杂原子 A 为氮或磷时，则 m 和 n 各为 0、1 或 2，条件是 m 和 n 之和为 2]，迄今尚未用于阴离子聚合，用作阴离子聚合引发剂，可轻松顺利地生成末端具有官能团的聚合物。
• HARADA, TOSHIRO;AKIBA, EIJI;OKU, AKIRA, TETRAHEDRON LETT., 1985, 26, N 5, 651-654
  作者：HARADA, TOSHIRO、AKIBA, EIJI、OKU, AKIRA

  DOI：——

  日期：——
• MARYANOFF, B. E.;REITZ, A. B.;DUHL-EMSWILER, B. A., J. AMER. CHEM. SOC., 1985, 107, N 1, 217-226
  作者：MARYANOFF, B. E.、REITZ, A. B.、DUHL-EMSWILER, B. A.

  DOI：——

  日期：——
• Process for producing polymer with functional end
  申请人：Satoh Kotaro

  公开号：US20070167587A1

  公开（公告）日：2007-07-19

  An organolithium compound represented by the following general formula (i): (i) [wherein A represents a heteroatom selected among oxygen, nitrogen, sulfur, and phosphorus; Ar represents optionally substituted aryl; R 1 represents C 1-10 alkyl; R 2 represents C 1-10 alkylene; R 3 represents C 1-10 alkyl or a protective group for the functional group -A-H (A is the heteroatom); and when the heteroatom A is oxygen or sulfur, then m and n each is 0 or 1, provided that the sum of m and n is 1, and when the heteroatom A is nitrogen or phosphorus, then m and n each is 0, 1, or 2, provided that the sum of m and n is 2], which has not hitherto been used in anionic polymerization, is used as an anionic polymerization initiator to easily and smoothly produce a polymer having a functional group at an end.