methyl (2R,1'R)-(-)-2(1'-hydroxyethyl)-allyl-acetate | 172342-30-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2R,1'R)-(-)-2(1'-hydroxyethyl)-allyl-acetate
• 英文别名: Methyl (2R)-2-[(1R)-1-hydroxyethyl]pent-4-enoate
• CAS: 172342-30-2
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: YGJTWICMMTYPFS-RNFRBKRXSA-N

物化性质

• 沸点：
  231.0±20.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  methyl (2R,1'R)-(-)-2(1'-hydroxyethyl)-allyl-acetate 在 palladium dihydroxide 吡啶 、 氢气 、 三甲基铝 、 三乙酰氧基硼氢化钠 、 caesium carbonate 、 臭氧 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 N-tert-Butoxy-N-((S)-1-{(R)-1-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-ethyl)-formamide
  参考文献：
  名称：

  Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00313-5
• 作为产物：
  描述：

  3-羟基丁酸甲酯 生成 methyl (2R,1'R)-(-)-2(1'-hydroxyethyl)-allyl-acetate
  参考文献：
  名称：

  NAKAMURA, KAORU;MIYAI, TAKEHIKO;NAGAR, ASHISH;OKA, SHINZABURO;OHNO, ATSUY+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1179-1187

  摘要：

  DOI：

文献信息

• Stereochemical Control in Microbial Reduction. 9. Diastereoselective Reduction of 2-Alkyl-3-oxobutanoate with Bakers’ Yeast
  作者：Kaoru Nakamura、Takehiko Miyai、Ashish Nagar、Shinzaburo Oka、Atsuyoshi Ohno

  DOI：10.1246/bcsj.62.1179

  日期：1989.4.15

  Bakers’ yeast reduces esters of 2-alkyl-3-oxobutanoic acid (CH3COCHRCO2R′; R=methyl, ethyl, propyl, propargyl, and allyl) into the corresponding (S)-hydroxy esters with exclusive stereoselectivity, while the configuration at the 2-position of the hydroxy esters is either S (anti) or R (syn) depending on the structure of the alkoxyl group in the carboalkoxyl moiety of the ester. Oftenly, the stereoselectivity

  面包师的酵母将 2-烷基-3-氧代丁酸（CH3COCHRCO2R'；R=甲基、乙基、丙基、炔丙基和烯丙基）的酯还原为相应的（S）-羟基酯，具有独特的立体选择性，而在 2羟基酯的-位是S(反)或R(syn)，这取决于酯的碳烷氧基部分中烷氧基的结构。通常，关于 2 位的立体选择性并不令人满意。一般来说，叔丁酯的还原在产物中占主导地位，而 1,1-二甲基丙酯的还原则发挥顺式优势。从酯的合理构象的角度讨论了这两种酯在非对映选择性方面的显着差异。
• Metachloropehoxybenzoic acid promoted stereoselective synthesis of 2,5-disubstituted tetrahydrofurans from α or γ-allyl-β-hydroxy esters: A formal synthesis of (±) methyl nonactate
  作者：Javed Iqbal、Anu Pandey、Bhanu P.S Chauhan

  DOI：10.1016/s0040-4020(01)86451-6

  日期：1991.1

  A one pot stereoselective synthesis of cis or trans 2,5-disubstituted tetrahydrofurans 3–8 can be achieved in high yields via electrophilic cyclisation of the corresponding cis or trans α or γ-allyl-β-hydroxyesters mediated by metachloroperoxybenzoic acid. The tetrahydrofurans 5 or 6 may be converted into (±) methyl nonactate by procedures described earlier. The role of methoxycarbonyl group during

  顺式或反式2,5-二取代的四氢呋喃的一锅立体选择性合成3 - 8可以以高的产率通过由metachloroperoxybenzoic酸介导的相应的顺式或反式或αγ-烯丙基-β羟基酯的电环化而实现。可以通过先前描述的方法将四氢呋喃5或6转化为（±）非乳酸甲酯。讨论了在这些环化过程中甲氧羰基的作用。
• Ring enlargement by alkylated 3-hydroxybutyrates: A synthesis of (12s, 13r)-(−)-12-methyl-13-tetradecanolide 1
  作者：Philip Kraft、Werner Tochtermann

  DOI：10.1016/0040-4020(95)00664-t

  日期：1995.10

  TBS-protected iodo alkohols 6 were prepared via Fráter alkylation and applied hi the synthesis of optically active macrohdes 5 and 10. By ring enlargement of cyclodecanone (7) the superposition molecule 5 of two macrocyclic odorants was synthesized and a conformationally fixed tricyclic macrolide11 constructed.

  TBS保护的碘醇6是通过Fráter烷基化制备的，并用于旋光大分子5和10的合成中。通过环癸癸酮（7）的环扩大，合成了两种大环臭味剂的叠加分子5，并构造了构象固定的三环大环内酯11。
• NAKAMURA, KAORU;MIYAI, TAKEHIKO;NAGAR, ASHISH;OKA, SHINZABURO;OHNO, ATSUY+, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1179-1187
  作者：NAKAMURA, KAORU、MIYAI, TAKEHIKO、NAGAR, ASHISH、OKA, SHINZABURO、OHNO, ATSUY+

  DOI：——

  日期：——
• Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)
  作者：James J.-W. Duan、Zhonghui Lu、Chu-Biao Xue、Xiaohua He、Jennifer L. Seng、John J. Roderick、Zelda R. Wasserman、Rui-Qin Liu、Maryanne B. Covington、Ronald L. Magolda、Robert C. Newton、James M. Trzaskos、Carl P. Decicco

  DOI：10.1016/s0960-894x(03)00313-5

  日期：2003.6

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.