cis-5-Cl-adamantan-2-ol | 77510-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-5-Cl-adamantan-2-ol
• 英文别名: trans-5-Cl-adamantan-2-ol；(E/Z)-5-chloroadamantan-2-ol；5-chloroadamantan-2-ol
• CAS: 77510-30-6
• 化学式: C₁₀H₁₅ClO
• 分子量: 186.681
• InChiKey: ZPDSKYXXCIKMJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  cis-5-Cl-adamantan-2-ol 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (E)-2-chloro-5-fluoroadamantane 、 (Z)-2-chloro-5-fluoroadamantane
  参考文献：
  名称：

  Transmission of polar substituent effects in the adamantane ring system as monitored by 19F NMR: hyperconjugation as a stereoinductive factor

  摘要：

  A limited series of (E)- and (Z)-5-substituted adamant-2-yl fluorides 8 and 9, respectively, has been synthesized and characterized, and the F-19 chemical shifts have been measured in several solvents. A wide range of F-19 substituent chemical shifts (SCS, ppm) are obtained for the former system (ca. 9.1 (c-C6H12), 9.6 (CDCl3), and 11.8 (HFIP)) compared to the latter (ca. 0.6 (c-C6H12), 0.7 (CDCl3), and 2.3 (HFIP)). Factorization of the F-19 SCS into polar field (rho-F-sigma-F) and residual contributions (F-19 SCS - rho-F-sigma-F) reveals the predominance of the latter solvent-independent component for the E fluorides (8). Comparison of 8 with a similar dissection of the F-19 SCS of 4-substituted bicyclo[2.2.2]oct-1-yl fluorides 2 strongly suggests that the origin of the large residual contributions for 8 is "through-three-bond" electron delocalization or double hyperconjugation. The importance of this long-range electronic mechanism as a factor governing pi-facial diastereoselection in 2,5-disubstituted adamantanes (1) is discussed. In particular, the assertion that the p-anilino substituent is an electron donor group at remote probe or reaction sites in saturated systems is addressed.

  DOI：

  10.1021/jo00010a012
• 作为产物：
  描述：

  4-Nitro-benzenesulfonic acid (1R,2S,3S,5S)-5-chloro-adamantan-2-yl ester 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 cis-5-Cl-adamantan-2-ol
  参考文献：
  名称：

  Charge dispersal in 1- and 2-adamantyl cations

  摘要：

  DOI：

  10.1016/s0040-4039(00)95337-1

文献信息

• N-SUBSTITUTED BENZAMIDES AND METHODS OF USE THEREOF
  申请人：XENON PHARMACEUTICALS INC.

  公开号：US20130317000A1

  公开（公告）日：2013-11-28

  The invention provides novel compounds having the general formula: and pharmaceutically acceptable salts thereof, wherein the variables R A , subscript n, ring A, X 2 , L, subscript m, X 1 , B, R 1 , R 2 , R 3 , R 4 , R 5 and R N have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  该发明提供了具有一般公式的新化合物：及其药用盐，其中变量RA、下标n、环A、X2、L、下标m、X1、B、R1、R2、R3、R4、R5和RN的含义如本文所述，并含有这种化合物和使用这种化合物和组合物的方法。
• N-substituted benzamides and methods of use thereof
  申请人：Genentech, Inc.

  公开号：US08952169B2

  公开（公告）日：2015-02-10

  The invention provides novel compounds having the general formula: and pharmaceutically acceptable salts thereof, wherein the variables RA, subscript n, ring A, X2, L, subscript m, X1, B, R1, R2, R3, R4, R5 and RN have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  该发明提供了具有以下一般式的新化合物及其药学上可接受的盐： 其中变量RA，下标n，环A，X2，L，下标m，X1，B，R1，R2，R3，R4，R5和RN具有如下所述的含义，以及含有此类化合物的组合物和使用此类化合物和组合物的方法。
• Giddings, Michael R.; Hudec, John, Canadian Journal of Chemistry, 1981, vol. 59, p. 459 - 467
  作者：Giddings, Michael R.、Hudec, John

  DOI：——

  日期：——
• GIDDING M. R.; HUDEC J., CAN. J. CHEM., 1981, 59, NO 2, 459-467
  作者：GIDDING M. R.、 HUDEC J.

  DOI：——

  日期：——