3-Cyclohexyl-3-hydroxy-buttersaeure-aethylester | 28811-84-9

• 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: 3-Cyclohexyl-3-hydroxy-buttersaeure-aethylester
• 英文别名: Ethyl-3-cyclohexyl-3-hydroxybutyrate；ethyl 3-cyclohexyl-3-hydroxybutanoate
• CAS: 28811-84-9
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: LGSDNBULYPOOTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  108-110 °C(Press: 2 Torr)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Cyclohexyl-3-hydroxy-buttersaeure-aethylester 在 二异丁基氢化铝 、 三氯氧磷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.97h， 生成 (E)-3-cyclohexylbut-2-en-1-ol
  参考文献：
  名称：

  基于辅助SN2'反应的四元立体中心的不对称构建：1,7-相对立体形成的案例

  摘要：

  The stereoselective construction of quaternary stereogenic centers is described that employs an allylic substitution through the intermediacy of a chiral carbamate leaving group. Five carbamates with two substituents at the allylic terminus combined with phenylcopper or n-butylcopper to provide alkenes in moderate to good yields and with moderate to high enantioselectivities at the newly created quaternary stereogenic center. The E-carbamate with methyl and cyclohexyl substituents at the gamma-terminus provided the highest yield (87%) and enantioselectivity (>99.9:0.1 er) of all the substitution patterns tested. The corresponding Z-carbamate gave the lowest enantioselectivity observed (80.0:20.0). Carbamates with other substituents (n-butyl and t-butyl) at the E-terminal position gave moderate yields and enantioselectivities of alkenes. Cinnamyl substrates also provided good yields of alkenes with moderate enantioselectivities. The origin of enantioselectivity is analyzed in the context of dimeric lithioheterocuprate structures.

  DOI：

  10.3987/com-13-s(s)82
• 作为产物：
  描述：

  ethyl 3-hydroxycrotonate 、 三环己基硼烷 以 苯 为溶剂， 生成 3-Cyclohexyl-3-hydroxy-buttersaeure-aethylester
  参考文献：
  名称：

  三烷基硼烷与β-二羰基化合物的光化学反应

  摘要：

  DOI：

  10.1016/s0040-4039(01)84536-6

文献信息

• A New Method for the Catalytic Aldol Reaction to Ketones
  作者：Kounosuke Oisaki、Yutaka Suto、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja034993n

  日期：2003.5.1

  A new method for the catalytic aldol reaction to ketones, using CuF.3PPh3.2EtOH complex as the catalyst and (EtO)3SiF as the additive, is described. The reaction can be applied to a wide range of ketones and trimethylsilyl enolates. On the basis of mechanistic studies, a working hypothesis for the catalytic cycle is proposed, in which the dynamic ligand exchange mediated by copper silicates produces

  介绍了一种以 CuF.3PPh3.2EtOH 配合物为催化剂、(EtO)3SiF 为添加剂的催化醛醇反应生成酮的新方法。该反应可应用于范围广泛的酮和三甲基甲硅烷基烯醇化物。在机理研究的基础上，提出了催化循环的工作假设，其中由硅酸铜介导的动态配体交换产生活性烯醇铜。此外，本反应可以扩展到使用 tol-BINAP 作为手性配体的催化对映选择性反应。
• Urazole analogs of prostaglandins
  申请人：Beecham Group Limited

  公开号：US04367338A1

  公开（公告）日：1983-01-04

  Compounds of formula (I) ##STR1## wherein: n is 1 to 5 Y is --CH.sub.2 --CH.sub.2 or --CH.dbd.CH--; R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1-12 carbon atoms; R.sub.2 is hydrogen, C.sub.1-4 alkyl, or phenyl; R.sub.3 is hydroxy or protected hydroxy; R.sub.4 is hydrogen, C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl --C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl moieties or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy or nitro groups; R.sub.5 is hydrogen, C.sub.1-6 alkyl, C.sub.5-8 cycloalkyl, phenyl, phenyl-C.sub.1-6 alkyl or phenyl C.sub.3-6 cycloalkyl, any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; or R.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and salts thereof are useful for their prostaglandin-like activity.

  式(I)的化合物##STR1##其中：n为1至5；Y为--CH.sub.2 --CH.sub.2或--CH.dbd.CH--; R.sub.1为氢或CO.sub.2；R.sub.1代表一个酯基，其中R.sub.1基团含有1-12个碳原子；R.sub.2为氢、C.sub.1-4烷基或苯基；R.sub.3为羟基或保护羟基；R.sub.4为氢、C.sub.1-9烷基、C.sub.3-8环烷基、C.sub.3-8环烷基-C.sub.1-6烷基、苯基、苯基--C.sub.1-6烷基、萘基、萘基C.sub.1-6烷基，其中苯基基团或萘基基团可以被一个或多个卤素、三氟甲基、C.sub.1-6烷基、羟基、C.sub.1-6烷氧基、苯基C.sub.1-6烷氧基或硝基取代；R.sub.5为氢、C.sub.1-6烷基、C.sub.5-8环烷基、苯基、苯基-C.sub.1-6烷基或苯基C.sub.3-6环烷基，其中苯基基团可以被一个或多个卤素、三氟甲基、C.sub.1-6烷基、C.sub.1-6烷氧基或硝基取代；或者R.sub.2和R.sub.4与它们连接的碳原子一起代表一个C.sub.5-8环烷基基团；以及其盐对于其前列腺素样活性是有用的。
• Synthesis of 3-hydroxy-3-cyclohexylbutyric acid derivatives. 2. Cyclic analogs of mevalonic acid
  作者：Germano Carganico、Paolo Cozzi、Gaetano Orsini

  DOI：10.1021/jm00366a021

  日期：1983.12

  The sodium salt of (Z)-3-hydroxy-3-(2-hydroxycyclohexyl)butyric acid (I) and its lactone (II) were prepared through the corresponding tert-butyl ester by hydrogenation, over Rh/Al2O3 catalyst, of the phenyl ring of tert-butyl 3-hydroxy-3-(2-hydroxyphenyl)butyrate (III). (Z)-3-Hydroxy-3-(2-methoxycyclohexyl)butyric acid was prepared similarly. (Z)-4-Methyloctahydro-2H-1-benzopyran-2-one was prepared

  （Z）-3-羟基-3-（2-羟基环己基）丁酸（I）及其内酯（II）的钠盐是通过相应的叔丁酯在Rh / Al2O3催化剂上加氢制得的。 3-羟基-3-（2-羟基苯基）丁酸叔丁酯的苯环（III）。类似地制备（Z）-3-羟基-3-（2-甲氧基环己基）丁酸。（Z）-4-甲基八氢-2H-1-苯并吡喃-2-酮是通过在Rh / Al2O3催化剂上加氢合成4-甲基香豆素的方法而制得的，4-香豆素是由III通过一锅法（包括水解，内酯化和脱水。上述化合物在5 X 10（-3）M时抑制乙酸盐掺入大鼠肝片中的胆固醇和脂肪酸中，但它们对HMG-CoA还原酶缺乏特异性抑制活性。
• Using urazole analogs of prostaglandins for bronchodilation
  申请人：Beecham Group Limited

  公开号：US04460595A1

  公开（公告）日：1984-07-17

  Compounds of the formula (I) ##STR1## wherein; n is 1 to 5 Y is --CH.sub.2 --CH.sub.2 or --CH.dbd.CH--; R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1-12 carbon atoms; R.sub.2 is hydrogen, C.sub.1-4 alkyl, or phenyl; R.sub.3 is hydroxy or protected hydroxy; R.sub.4 is hydrogen, C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl -C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl moieties or naphthyl moieties may be substituted by one or more halogen trifluoromethyl, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy or nitro groups; R.sub.5 is hydrogen, C.sub.1-6 alkyl, C.sub.5-8 cycloalkyl, phenyl, phenyl-C.sub.1-6 alkyl or phenyl C.sub.3-6 cycloalkyl, any of which phenyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; or R.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and salts thereof are useful for their prostaglandin-like activity.

  化合物的公式（I）## STR1 ##其中; n为1到5，Y为--CH.sub.2--CH.sub.2或--CH.dbd.CH--; R.sub.1为氢或CO.sub.2 R.sub.1代表一个酯基，在其中R.sub.1基团含有1-12个碳原子; R.sub.2为氢，C.sub.1-4烷基或苯基; R.sub.3为羟基或保护羟基; R.sub.4为氢，C.sub.1-9烷基，C.sub.3-8环烷基，C.sub.3-8环烷基-C.sub.1-6烷基，苯基，苯基-C.sub.1-6烷基，萘基，萘基C.sub.1-6烷基，其中任何苯基基团或萘基基团均可被一个或多个卤素三氟甲基，C.sub.1-6烷基，羟基，C.sub.1-6烷氧基，苯基C.sub.1-6烷氧基或硝基基团取代; R.sub.5为氢，C.sub.1-6烷基，C.sub.5-8环烷基，苯基，苯基-C.sub.1-6烷基或苯基C.sub.3-6环烷基，其中任何苯基基团均可被一个或多个卤素，三氟甲基，C.sub.1-6烷基，C.sub.1-6烷氧基或硝基基团取代; 或R.sub.2和R.sub.4与它们连接的碳原子一起代表一个C.sub.5-8环烷基; 以及它们的盐对于它们的前列腺素样活性是有用的。
• Simple Analogs of the Antiarthritic Steroids¹
  作者：Domenick Papa、Helen F. Ginsberg、Frank J. Villani

  DOI：10.1021/ja01646a047

  日期：1954.9