6-cyanohex-2-ynyl mesylate | 77493-17-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 6-cyanohex-2-ynyl mesylate
• 英文别名: 1-Methanesulphonyloxy-6-cyano-hex-2-yne；6-cyanohex-2-ynyl methanesulfonate
• CAS: 77493-17-5
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: BRHXEBKLRZRVBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-cyanohex-2-ynyl mesylate 在 Lindlar's catalyst 吡啶 、 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 15.5h， 生成 trans-2-(6-cyanohexyl)-3-(methoxycarbonyl)cyclopentanone
  参考文献：
  名称：

  Prostaglandins. 3. Synthetic approaches to 11-deoxyprostaglandins

  摘要：

  DOI：

  10.1021/jo00133a029
• 作为产物：
  描述：

  6-chloro-2-hexyn-1-ol 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.92h， 生成 6-cyanohex-2-ynyl mesylate
  参考文献：
  名称：

  Prostaglandins. 3. Synthetic approaches to 11-deoxyprostaglandins

  摘要：

  DOI：

  10.1021/jo00133a029

文献信息

• Regiocontrolled Cu^I-Catalyzed Borylation of Propargylic-Functionalized Internal Alkynes
  作者：Abraham L. Moure、Ramón Gómez Arrayás、Diego J. Cárdenas、Inés Alonso、Juan C. Carretero

  DOI：10.1021/ja300627s

  日期：2012.5.2

  orbitalic influence from the propargylic group, matched with ligand and substrate size effects, as key factors involved in the high β-selectivity. The vinylboronates allowed the stereoselective synthesis of trisubstituted olefins, while allylic substitution of the SO(2)Py group without affecting the boronate group provided access to formal hydroboration products of unbiased dialkylalkynes.

  在铜（I）催化的二烷基内炔与双（频哪醇）二硼的硼化中已经实现了良好的反应性和区域控制。炔丙基极性基团（OH、OR、SAr、SO(2)Ar 或 NHTs）的存在，与作为配体的 PCy(3) 结合，可以最大限度地提高反应性和位点选择性（β 对炔丙基功能）。DFT 计算表明来自炔丙基的微妙轨道影响与配体和底物尺寸效应相匹配，是高β-选择性的关键因素。乙烯基硼酸酯允许立体选择性合成三取代烯烃，而 SO(2)Py 基团的烯丙基取代而不影响硼酸酯基团提供了获得无偏二烷基炔烃的正式硼氢化产物的途径。
• Terminal amino prostaglandin analogues
  申请人：Beecham Group Limited

  公开号：US04315022A1

  公开（公告）日：1982-02-09

  Compounds of the formula (I): ##STR1## having pharmacological activities similar to those of natural prostaglandins wherein: n is 0 to 5; X is CO, CS or CH.sub.2 ; Y is --CH.sub.2 --CH.sub.2 --; or, when n is 1 to 5, --CH.dbd.CH-- or --C.tbd.C--; R.sub.1 is either CH.sub.2 NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are separately hydrogen or C.sub.1-6 alkyl, or R.sub.5 is hydrogen and R.sub.6 is (CH.sub.2).sub.m CO.sub.2 R.sup.1.sub.9 wherein m is 0 to 4 and R.sup.1.sub.9 is optionally substituted C.sub.1-6 alkyl or benzyl, optionally substituted in the phenyl ring by chlorine or bromine atoms or by nitro or CF.sub.3 groups; or R.sub.5 and R.sub.6 are both the same (CH.sub.2).sub.m CO.sub.2 R.sup.1.sub.9 as hereinbefore defined; or C(NH.sub.2).dbd.NOH; or C(OR.sub.7).dbd.NH.sub.2.sup.+ B.sup.- wherein R.sub.7 is C.sub.1-6 alkyl and B.sup.- is a salting ion; or CH.sub.2 NHR.sub.8, wherein R.sub.8 is SO.sub.2 R.sup.1.sub.9, COR.sup.1.sub.9 or CZNHR.sub.9 and R.sup.1.sub.9 is as hereinbefore defined, R.sub.9 is hydrogen or C.sub.1-6 alkyl and Z is oxygen or sulphur; or CZNH.sub.2 wherein Z is as hereinbefore defined: R.sub.2 is hydrogen or C.sub.1-4 alkyl; R.sub.3 is C.sub.1-9 alkyl, C.sub.5-8 cycloalkyl or C.sub.5-8 cycloalkyl --C.sub.1-6 alkyl; or R.sub.2 and R.sub.3 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and R.sub.4 is hydrogen or C.sub.1-6 alkyl; and salts thereof; with the provisos (i) that when X is CH.sub.2 then Y must be --CH.sub.2 --CH.sub.2 --, and (ii) when R.sub.1 is CH.sub.2 NR.sub.5 R.sub.6 or CH.sub.2 NHR.sub.8 then Y must be --CH.sub.2 --CH.sub.2 --, pharmaceutical compositions containing them and processes for their preparation.

  化合物的公式(I): ##STR1## 具有类似于天然前列腺素的药理活性，其中：n为0至5; X为CO，CS或CH.sub.2; Y为--CH.sub.2--CH.sub.2--; 或者，当n为1至5时，为--CH.dbd.CH--或--C.tbd.C--; R.sub.1为CH.sub.2NR.sub.5R.sub.6，其中R.sub.5和R.sub.6分别为氢或C.sub.1-6烷基，或R.sub.5为氢，R.sub.6为(CH.sub.2).sub.mCO.sub.2R.sup.1.sub.9，其中m为0至4，R.sup.1.sub.9为选择性取代的C.sub.1-6烷基或苄基，选择性取代苯环上可以是氯或溴原子或硝基或CF.sub.3基团；或者R.sub.5和R.sub.6均为(CH.sub.2).sub.mCO.sub.2R.sup.1.sub.9，如前所述；或C(NH.sub.2).dbd.NOH; 或C(OR.sub.7).dbd.NH.sub.2.sup.+ B.sup.-，其中R.sub.7为C.sub.1-6烷基，B.sup.-为盐基离子；或CH.sub.2NHR.sub.8，其中R.sub.8为SO.sub.2R.sup.1.sub.9，COR.sup.1.sub.9或CZNHR.sub.9，R.sup.1.sub.9如前所述，R.sub.9为氢或C.sub.1-6烷基，Z为氧或硫；或CZNH.sub.2，其中Z如前所述：R.sub.2为氢或C.sub.1-4烷基；R.sub.3为C.sub.1-9烷基，C.sub.5-8环烷基或C.sub.5-8环烷基--C.sub.1-6烷基；或R.sub.2和R.sub.3与它们连接的碳原子一起表示C.sub.5-8环烷基；R.sub.4为氢或C.sub.1-6烷基；及其盐；但是，当X为CH.sub.2时，Y必须为--CH.sub.2--CH.sub.2--，且当R.sub.1为CH.sub.2NR.sub.5R.sub.6或CH.sub.2NHR.sub.8时，Y必须为--CH.sub.2--CH.sub.2--，包含它们的制药组合物和制备它们的方法。
• Imidazole derivatives, their preparation and their pharmaceutical compositions
  申请人：BEECHAM GROUP PLC

  公开号：EP0020039A1

  公开（公告）日：1980-12-10

  Compounds of the formula (I): wherein: n is 0 to 5; X is CO, CS or CH2; Y is -CH2H2-; or, when n is 1 to 5, -CH=CH- or -C≡C-; R1 is either CH2NR5R6, wherein R5 and R6 are separately hydrogen or C1-6 alkyl, or Rs is hydrogen and R6 is (CH2)mCO2R19 wherein m is 0 to 4 and R19 is optionally substituted C1-6 alkyl or benzyl, optionally substituted in the phenyl ring by chlorine or bromine atoms or by nitro or CF3 groups; or R5 and R6 are both the same (CH2)mCO2R19 aa hereinbefore defined; or C(NH2)=NOH; or C(OR7)=NH2B wherein R1 is C1-6 alkyl and B- is a salting ion; or CH2NHR8, wherein RB is SO2R'9, COR19, or CZNHR9 and R19 is as hereinbefore defined, R9 is hydrogen or C1-6 alkyl and Z is oxygen or sulphur; or CZNH2 wherein Z is as hereinbefore defined: R2 is hydrogen or C1-4 alkyl; R3 is C1-9 alkyl, C5-8 cycloalkyl or C5-8 cycloalkyl -C1-6 alkyl; or R2 and R3 taken with the carbon atom to which they are joined represent a C5-8 cycloalkyl group; and R4 is hydrogen or Cl-6 alkyl; and salts thereof; with the provisos (i) that when X is CH2 then Y must be -CH2-CH2-, and (ii) when R, is CH2NRsR6 or CH2NHR8 then Y must be -CH2-CH2-, pharmaceutical compositions containing them and processes for their preparation.

  式 (I) 的化合物： 其中 n 为 0 至 5； X 是 CO、CS 或 CH2 Y 是-CH2H2-；或者，当 n 为 1 至 5 时，-CH=CH- 或-C≡C-； R1 是 CH2NR5R6，其中 R5 和 R6 分别是氢或 C1-6 烷基，或 Rs 是氢，R6 是 (CH2)mCO2R19，其中 m 是 0 至 4，R19 是任选取代的 C1-6 烷基或苄基，在苯基环上任选被氯或溴原子或硝基或 CF3 基团取代；或 R5 和 R6 同为上文定义的 (CH2)mCO2R19 aa；或 C(NH2)=NOH；或 C(OR7)=NH2B，其中 R1 为 C1-6 烷基，B- 为盐离子；或 CH2NHR8，其中 RB 为 SO2R'9、COR19 或 CZNHR9，R19 如前定义，R9 为氢或 C1-6 烷基，Z 为氧或硫；或 CZNH2，其中 Z 如前定义： R2 是氢或 C1-4 烷基； R3是C1-9烷基、C5-8环烷基或C5-8环烷基-C1-6烷基；或 R2 和 R3 与它们连接的碳原子一起代表一个 C5-8 环烷基；以及 R4是氢或Cl-6烷基；及其盐类；但书(i)当X是CH2时，Y必须是-CH2-CH2-，(ii)当R是CH2NRsR6或CH2NHR8时，Y必须是-CH2-CH2-，含有它们的药物组合物及其制备工艺。
• WHITE, W. L.;ANZEVENO, P. B.
  作者：WHITE, W. L.、ANZEVENO, P. B.

  DOI：——

  日期：——
• US4315022A
  申请人：——

  公开号：US4315022A

  公开（公告）日：1982-02-09