(E)-1-Cyclohexyl-2-hepten-1-ol | 145526-93-8

• 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)-1-Cyclohexyl-2-hepten-1-ol
• 英文别名: (2E)-1-cyclohexyl-2-hepten-1-ol；(E)-1-cyclohexylhept-2-en-1-ol
• CAS: 145526-93-8
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: KNMUZFWFGPQFHD-DHZHZOJOSA-N

物化性质

• 沸点：
  269.7±8.0 °C(predicted)
• 密度：
  0.910±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  二碘甲烷 、 (E)-1-Cyclohexyl-2-hepten-1-ol 在 三氢化钐 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(R*)-<(1R*,2R*)-1,2-Methanohexyl>cyclohexylmethanol
  参考文献：
  名称：

  Diastereoselectivity in the Cyclopropanation of 3,3-Bimetallic Allylic Alcohols. Preparation of Diastereomeric Cyclopropyl Carbinols via a Simple Oxidation-Reduction Sequence

  摘要：

  A highly diastereoselective cyclopropanation of allylic alcohols, containing a silyl and/or stannyl group using samarium/dihalomethane, provides a variety of bimetallic cyclopropane carbinols in good yield. A comparison with the more traditional Simmons-Smith conditions and its variants is made. The diastereoselectivity varies from 1:10 to >50:1 and depends on the substituents on the carbinol side chain (R-group) and on the substituents on the alkene portion of the allylic alcohol. Excellent diastereoselectivity (>50:1) was always obtained whenever a eis-substituent was present. Moreover, the minor diastereomer from the cyclopropanation can easily be obtained via a simple oxidation of the major cyclopropyl carbinol, followed by a selective reduction of the corresponding cyclopropyl ketone. Using LiAlH4 at 0 degrees C, facial selectivities of 15 to 20:1 are obtained for this reduction, while slightly higher selectivities up to (29:1) can be obtained using DIBAL-H. The combination of the cyclopropanation and oxidation/selective reduction sequence provides access to both diastereomeric bimetallic cyclopropanes.

  DOI：

  10.1021/jo00113a031
• 作为产物：
  描述：

  (E)-2-庚烯醛 、 环己氯化镁 以 乙醚 为溶剂， 生成 (E)-1-Cyclohexyl-2-hepten-1-ol
  参考文献：
  名称：

  无环烯丙基磷酸酯与有机铜试剂的立体选择反应。

  摘要：

  一系列具有一般结构R（1）CH == CHCH（OH）R（2）的无环烯丙基醇通过Sharpless动力学拆分得到解析。这些对映异构体富集的醇的羟基被衍生为磷酸二乙酯，并使衍生物与有机铜试剂反应。用试剂R（3）（2）CuCNLi（2）观察到最干净的取代反应。当R（1）= Me，R（3）= n-Bu时，R（2）的大小会影响位移的区域选择性和立体选择性。较大的R（2）组具有较高的区域选择性和立体选择性：R（2）= 3-戊基时，观察到> 98％的S（N）2'区域选择性和> 98％的抗立体选择性。Bn（2）CuCNLi（2）的立体选择性可与n-Bu（2）CuCNLi（2）观察到的相当，但t-Bu（2）CuCNLi（2）表现出低得多的非对映优先性。

  DOI：

  10.1021/jo0104431

文献信息

• AgAsF6 as safe alternative to AgClO4 for generating cationic zirconocene species: Utilities in lewis acid-promoted selective CC bond forming reactions
  作者：Keisuke Suzuki、Takayuki Hasegawa、Takahiro Imai、Hideki Maeta、Shigeru Ohba

  DOI：10.1016/0040-4020(94)01135-m

  日期：1995.4

  synthesis, AgAsF6 proved to be an efficient catalyst that serves as a safe alternative to AgClO4. Scope and limitation is discussed on this new catalyst in the processes including (1) alkyl/alkenyl transfer reaction from organozirconocene chloride to aldehyde, (2) two- and four-carbon homologation of aldehyde, (3) dual synthetic methods of 1,3-dienes from aldehydes/ketones via 1,3-bimetallic species

  为了产生可用于有机合成的阳离子锆茂金属物种，AgAsF 6被证明是一种有效的催化剂，可作为AgClO 4的安全替代品。讨论了这种新型催化剂在工艺上的范围和局限性，这些工艺包括：（1）从有机锆茂氯化物到醛的烷基/烯基转移反应；（2）醛的二碳和四碳同系化；（3）1,3的双重合成方法醛/酮通过1，3-双金属物种生成二烯二烯，以及（4）通过邻喹二甲烷物种生成三组分烷基化环加成。
• Inter- and Intramolecular Additions of 1-Alkenylboronic Acids or Esters to Aldehydes and Ketones Catalyzed by Rhodium(I) Complexes in Basic, Aqueous Solutions
  作者：Norio Miyaura、Akinori Takezawa、Kenji Yamaguchi、Toshimichi Ohmura、Yasunori Yamamoto

  DOI：10.1055/s-2002-34219

  日期：——

  Grignard-type addition reaction of 1-alkenylboronic acids or their esters to aldehydes or ketones were carried out in aqueous MeOH or DME in the presence of KOH ( 1 equivalent) and an RhCl(dppf) or Rh(OH)(dppf) catalyst (3 mol%). The utility of the protocol was demonstrated in the corresponding intramolecular reaction giving cyclic homoallylic alcohols.

  在 KOH（1 当量）和 RhCl(dppf) 或 Rh(OH)(dppf) 催化剂存在下，在 MeOH 或 DME 水溶液中进行 1-烯基硼酸或其酯与醛或酮的格氏型加成反应（ 3 摩尔％）。该协议的效用在相应的分子内反应中得到了证明，给出了环状 homoallylic 醇。
• Grignard-type addition of alkenyl- and alkylzirconocene chloride to aldehyde: Remarkable catalytic acceleration effect of AgClO4
  作者：Hideki Maeta、Takeshi Hashimoto、Takayuki Hasegawa、Keisuke Suzuki

  DOI：10.1016/s0040-4039(00)61101-2

  日期：1992.9

  Nucleophilic addition of alkenylzirconocene chloride [Cp2Zr(Cl)CH=CHR] to aldehyde, which is ordinarily a slow reaction, is remarkably accelerated by a catalytic amount of AgClO4. The rate acceleration effect is also valid for the alkyl congener, Cp2Zr(Cl)R.