(R)-2-methylsuccinate-1-monomethyl ester | 83509-04-0

• 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: (R)-2-methylsuccinate-1-monomethyl ester
• 英文别名: (R)-methyl-succinic acid-1-methyl ester；(R)-Methyl-bernsteinsaeure-1-methylester；(R)-4-Methoxy-3-methyl-4-oxobutanoic acid；(3R)-4-methoxy-3-methyl-4-oxobutanoic acid
• CAS: 83509-04-0
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: QEZMQNIFDRNSJZ-SCSAIBSYSA-N

物化性质

• 沸点：
  248.8±23.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-methylsuccinate-1-monomethyl ester 在 正丁基锂 、 2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine 、 palladium 10% on activated carbon 、 sodium hydride 、 对甲苯磺酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 45.0h， 生成
  参考文献：
  名称：

  青蒿素的合成方法

  摘要：

  本发明公开了一种青蒿素的合成方法。目前青蒿素主要从植物青蒿中分离提取得到，由于青蒿中青蒿素含量极低，加上青蒿的种植又会受自然灾害、地理条件和种植技术等因素的影响，青蒿素价格昂贵。已知的青蒿素全合成方法都有合成路线长、原料成本高、反应条件苛刻和难以放大生产等缺点。本发明提供一种合成路线短、原料成本低、反应条件温和、可放大生产的青蒿素新全合成方法。

  公开号：

  CN104119353B
• 作为产物：
  描述：

  (R)-(+)-甲基丁二酸 在 氢氧化钾 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 50.0h， 生成 (R)-2-methylsuccinate-1-monomethyl ester
  参考文献：
  名称：

  Derivatives of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline: effect of changes at postions 2 and 5 of the hexanoic acid portion

  摘要：

  Several derivatives of the potent angiotensin converting enzyme inhibitor 5(S)-benzamido-4-oxo-6-phenylhexanoyl-L-proline (1) were synthesized and tested for converting enzyme inhibition activity and blood pressure lowering effects in rats. One compound, 5(S)-benzamido-2(R)-methyl-4-oxo-6-phenylhexanoyl-L-proline (2a), had and I50 against angiotensin converting enzyme of 1.0 x 10(-9) M and is the most potent inhibitor prepared thus far in this class of compounds. Testing of 2a orally at 30 mg/kg for inhibition of the angiotensin I induced blood pressure increase in conscious normotensive rats gave 100% inhibition that required 143 min before the angiotensin I blood pressure response returned to 70% of the pretreatment control response. In the conscious renal hypertensive rat, 2a given orally at a dose of 3 mg/kg caused a lowering of blood pressure that reached its maximum of 40 mmHg 8 h following drug administration.

  DOI：

  10.1021/jm00353a005

文献信息

• Design and synthesis of a novel three-hindered quadrant bisphosphine ligand and its application in asymmetric hydrogenation
  作者：Kexuan Huang、Xiaowei Zhang、Thomas J. Emge、Guohua Hou、Bonan Cao、Xumu Zhang

  DOI：10.1039/c0cc02620d

  日期：——

  A novel three hindered quadrant bisphosphine ligand has been synthesized. The ligand shows excellent enantioselectivities and reactivities for rhodium-catalyzed hydrogenations of various functionalized olefins.

  合成了一种新型三阻碍四分之一双膦配体。该配体在铑催化的各种功能化烯烃氢化反应中表现出优异的对映选择性和反应活性。
• Highly Enantioselective Rhodium-Catalyzed Hydrogenation of 2-(2-Methoxy-2-oxoethyl)acrylic Acid− A Convenient Access of Enantiomerically Pure Isoprenoid Building Blocks
  作者：Markus Ostermeier、Bernhard Brunner、Christian Korff、Günter Helmchen

  DOI：10.1002/ejoc.200300222

  日期：2003.9

  Asymmetric catalytic hydrogenation of 2-(2-methoxy-2-oxoethyl)acrylic acid (5) to give (2S)-4-methoxy-2-methyl-4-oxobutanoic acid [(S)-6] was studied. An enantiomeric excess of 99.7% ee was achieved with a catalyst formed in situ from [Rh(COD)2]BF4 and the chiral phosphite L2 in 1,2-dichloroethane as solvent. In addition, enzyme-catalyzed semi-saponification of dimethyl 2-methylsuccinate was investigated

  研究了 2-(2-甲氧基-2-氧乙基) 丙烯酸 (5) 的不对称催化氢化得到 (2S)-4-甲氧基-2-甲基-4-氧代丁酸 [(S)-6]。使用由 [Rh(COD)2]BF4 和手性亚磷酸酯 L2 在作为溶剂中的 [Rh(COD)2]BF4 和手性亚磷酸酯 L2 原位形成的催化剂，实现了 99.7% ee 的对映体过量。此外，还研究了酶催化的 2-甲基琥珀酸二甲酯的半皂化反应。单酯 (S)-6 被转化为一些化合物，这些化合物可以作为天然产物合成中的 C5 结构单元。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Highly Enantioselective Hydrogenation of α-Dehydroamino Esters and Itaconates with Triphosphorous Bidentate Ligands and the Unprecedented Solvent Effect Thereof
  作者：Weicheng Zhang、Xumu Zhang

  DOI：10.1021/jo0622429

  日期：2007.2.1

  coordination in a Pd(II) complex of a phosphine-phosphoramidite ligand 1, which showed excellent enantioselectivity (up to 99.4% ee) in Rh-catalyzed hydrogenation of α-dehydroamino esters in acetone. A dramatic solvent effect was found in the hydrogenation of itaconates, which induces opposite chiralities of the product with the same catalytic system by the use of different solvents (e.g., 99.6% ee (R) in TFE

  X射线衍射实验表明，膦-亚磷酰胺配体1的Pd（II）络合物中有趣的三磷二齿配位，在Rh催化的丙酮中α-脱氢氨基酯的加氢反应中表现出出色的对映选择性（高达99.4％ee）。 。在衣康酸酯的氢化中发现了显着的溶剂效应，通过使用不同的溶剂（例如，TFE中的99.6％ee（R）与甲基中的71.2％ee（S），在相同的催化体系下诱导了相反的手性乙基酮）。
• Ruthenium (II)-BINAP complex catalyzed asymmetric hydrogenation of unsaturated dicarboxylic acids
  作者：Hiroyuki Kawano、Youichi Ishii、Takao Ikariya、Mahiko Saburi、Sadao Yoshikawa、Yasuzo Uchida、Hidenori Kumobayashi

  DOI：10.1016/s0040-4039(00)96006-4

  日期：1987.1

  Asymmetric hydrogenation of unsaturated dicarboxylic acids employing ruthenium-BINAP complexes as catalyst gave optically active 2-alkylsuccinic acids with high enantioselectivities.

  使用钌-BINAP配合物作为催化剂对不饱和二羧酸进行不对称氢化，得到具有高对映选择性的光学活性2-烷基琥珀酸。
• Hybrid P-chiral diphosphines for asymmetric hydrogenation
  作者：Duncan Carmichael、Henri Doucet、John M. Brown

  DOI：10.1039/a808711c

  日期：——

  A family of diphosphine ligands has been prepared by Michael addition of o-anisylphenyl phosphide to diethyl vinylphosphonate and elaboration to phospholanes based on hexane-2,5-diol or mannitol; some preliminary results of Rh-complex catalysed hydrogenations are reported.

  一种双膦配体家族通过o-亚硝苯基磷化物与二乙基乙烯磷酸酯的迈克尔加成反应制备而成，并进一步构造为基于己烷-2,5-二醇或甘露醇的磷烷；报告了一些由Rh-配合物催化的加氢反应的初步结果。