(2RS,3SR)-2-amino-3-cyclohexyl-3-hydroxy-propionic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2RS,3SR)-2-amino-3-cyclohexyl-3-hydroxy-propionic acid
• 英文别名: (2RS,3SR)-2-Amino-3-cyclohexyl-3-hydroxy-propionsaeure；(2R,3S)-2-amino-3-cyclohexyl-3-hydroxypropanoic acid
• 化学式: C₉H₁₇NO₃
• 分子量: 187.239
• InChiKey: MPPSCQJRTVSDRL-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,3SR)-2-amino-3-cyclohexyl-3-hydroxy-propionic acid 在 盐酸 、 20 % Pd(OH)2/C 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 生成 (3R)-1-butyl-3-[(S)-cyclohexyl(hydroxy)methyl]-1,4,9-triazaspiro[5.5]undecane-2,5-dione
  参考文献：
  名称：

  Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate

  摘要：

  Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compound 2. Structural hybridation of 4 with the orally available analog 5 resulted in another orally-available spirodiketopiperazine CCR5 antagonist 6a that possesses more favorable pharmaceutical profile for use as a drug candidate. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.109
• 作为产物：
  描述：

  (2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester 在 盐酸 、 乙醇 、 镍 作用下， 生成 (2RS,3SR)-2-amino-3-cyclohexyl-3-hydroxy-propionic acid
  参考文献：
  名称：

  抗生素及相关物质研究。四、DL-threo-β-Cyclohexylserine 和 DL-threo-2-Dichloroacetamido-1-cyclohexylpropane-1,3-diol 的合成

  摘要：

  (1) Erlenmeyer苯丝氨酸的N-乙酰乙酯在阮内镍催化剂上用氢气还原，得到DL-苏式-N-乙酰-β-环己基丝氨酸乙酯，粗收率高达86.8%。随后用稀盐酸水解得到 DL-苏-β-环己基丝氨酸，通过高碘酸盐氧化得到六氢苯甲醛。(2) DL-threo-β-环己基丝氨酸乙酯的阮内镍还原得到DL-threo-2-amino-1-cyclohexylpropane-1, 3-diol。氨基醇被转化为 DL-threo-2-dichloroacetamido-1-cyclohexylpropane-1,3-diol，一种氯霉素类似物。

  DOI：

  10.1246/bcsj.29.987

文献信息

• Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile
  作者：Haitao Zhu、Pinhong Chen、Guosheng Liu

  DOI：10.1021/ja412023b

  日期：2014.2.5

  A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.
• Studies on Antibiotics and Related Substances. IV. Synthesis of DL-threo-β-Cyclohexylserine and DL-threo-2-Dichloroacetamido-1-cyclohexylpropane-1,3-diol
  作者：Sumio Umezawa、Yoshihisa Oguma

  DOI：10.1246/bcsj.29.987

  日期：1956.9

  When the N-acetyl ethyl ester of Erlenmeyer’s phenylserine was reduced with hydrogen over Raney nickel catalyst, ethyl DL-threo-N-acetyl-β-cyclohexylserinate was obtained in crude yields as high as 86.8 %. Subsequent hydrolysis with dilute hydrochloric acid afforded DL-threo-β-cyclohexylserine, which gave hexahydrobenzaldehyde by periodate oxidation. (2) Raney nickel reduction of ethyl DL-threo-β-cyclohexyl-serinate

  (1) Erlenmeyer苯丝氨酸的N-乙酰乙酯在阮内镍催化剂上用氢气还原，得到DL-苏式-N-乙酰-β-环己基丝氨酸乙酯，粗收率高达86.8%。随后用稀盐酸水解得到 DL-苏-β-环己基丝氨酸，通过高碘酸盐氧化得到六氢苯甲醛。(2) DL-threo-β-环己基丝氨酸乙酯的阮内镍还原得到DL-threo-2-amino-1-cyclohexylpropane-1, 3-diol。氨基醇被转化为 DL-threo-2-dichloroacetamido-1-cyclohexylpropane-1,3-diol，一种氯霉素类似物。
• Spirodiketopiperazine-based CCR5 antagonist: Discovery of an antiretroviral drug candidate
  作者：Rena Nishizawa、Toshihiko Nishiyama、Katsuya Hisaichi、Chiaki Minamoto、Naoki Matsunaga、Yoshikazu Takaoka、Hisao Nakai、Stephen Jenkinson、Wieslaw M. Kazmierski、Hideaki Tada、Kenji Sagawa、Shiro Shibayama、Daikichi Fukushima、Kenji Maeda、Hiroaki Mitsuya

  DOI：10.1016/j.bmcl.2010.12.109

  日期：2011.2

  Following the discovery that hydroxylated derivative 3 (Fig. 1) was one of the oxidative metabolites of the original lead 1, it was found that hydroxylated compound 4 possesses higher in vitro anti-HIV potency than the corresponding non-hydroxylated compound 2. Structural hybridation of 4 with the orally available analog 5 resulted in another orally-available spirodiketopiperazine CCR5 antagonist 6a that possesses more favorable pharmaceutical profile for use as a drug candidate. (c) 2010 Elsevier Ltd. All rights reserved.