(2R,3S)-2,3-dihydroxy-3-(3,4-methylenedioxyphenyl)propionate | 426814-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (2R,3S)-2,3-dihydroxy-3-(3,4-methylenedioxyphenyl)propionate
• 英文别名: ethyl (2R,3S)-2,3-dihydroxy-3-[(3',4'-methylenedioxy)phenyl]propanoate；(2R,3S)-ethyl 3-(benzo[d][1,3]dioxol-6-yl)-2,3-dihydroxypropanoate；ethyl (2R,3S)-3-(1,3-benzodioxol-5-yl)-2,3-dihydroxypropanoate
• CAS: 426814-32-6
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: PJRRVZLKOQMCJA-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3-dihydroxy-3-(3,4-methylenedioxyphenyl)propionate 在 氯化亚砜 、 三乙胺 作用下， 反应 0.75h， 生成 (R)-2-氨基-3-(苯并[D][1,3]二氧杂-5-基)丙酸
  参考文献：
  名称：

  Asymmetric synthesis of l-DOPA and (R)-selegiline via, OsO4-catalyzed asymmetric dihydroxylation

  摘要：

  A simple and effective procedure for the enantioselective synthesis of two important neurotransmitter drugs, hat is, (S)-3,4-dihydroxyphenylalanine (L-DOPA) and (R)-N,alpha-dimethyl-N-2-propynylbenzeneethaneamine [(R)-selegiline], is described by employing the Sharpless asymmetric dihydroxylation (AD) as a key step to introduce chirality. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.08.007
• 作为产物：
  描述：

  (E)-3-(1,3-苯并二氧戊环-5-基)丙烯酸乙酯 在 potassium osmate(VI) 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 以92%的产率得到(2R,3S)-2,3-dihydroxy-3-(3,4-methylenedioxyphenyl)propionate
  参考文献：
  名称：

  CoCl 2 - NaBH 4催化硝基环亚硫酸盐的还原环化反应不对称合成四氢喹啉-3-醇

  摘要：

  已经描述了具有高光学纯度的基于不对称二羟基化和CoCl 2催化的硝基环亚硫酸盐与NaBH 4的还原性环化来构建手性3-取代的四氢喹啉衍生物的新方法。该方法已成功地用于PNU 95666E和安那奇林H发色团的形式合成。

  DOI：

  10.1021/ol8028109

文献信息

• Stereoselective and Regioselective Reaction of Cyclic Ortho Esters with Phenols
  作者：Joseph J. Bozell、Darrin Miller、Bonnie R. Hames、Cheryl Loveless

  DOI：10.1021/jo005736t

  日期：2001.5.1

  treated with BF(3) x OEt(2) at room temperature, but C-addition products are stable under the same conditions. X-ray structural analysis of the C-addition compound indicates that its stereochemistry is opposite to that observed in reaction of similar ortho esters with chloride from TMSCl. However, the stereochemistry of the reaction can be rationalized by the ability of the ortho ester to isomerize via an

  当在低温下用BF（3）x OEt（2）处理时，环状原酸酯会与酚发生立体选择性和区域选择性反应。苯酚对原酸酯的侵蚀发生在苯酚上给电子基团的开放碳对位（“ C加成”）或酚羟基（“ O加成”），具体取决于所形成阳离子的性质从原酸酯和BF（3）x OEt（2）的反应中获得。如果在室温下用BF（3）x OEt（2）处理，则由O加成产生的产物会还原为起始酚，C加成产物和O加成产物的混合物，但C加成产物在相同的条件。C-加成化合物的X射线结构分析表明，其立体化学与相似的原酸酯与来自TMSC1的氯化物反应中观察到的立体化学相反。
• The asymmetric synthesis of β-aryl-α-hydroxy esters from β-aryl-α,β-dihydroxy esters
  作者：Nicholas J Lawrence、Stephen Brown

  DOI：10.1016/s0040-4020(01)01176-0

  日期：2002.1

  alpha,beta-Dihydroxy-beta-aryl esters obtained via Sharpless asymmetric dihydroxylation (AD) of substituted cinnamate esters are reduced by sequential reaction with trimethyl orthoacetate and acetyl bromide followed by catalytic hydrogenolysis in methanol to give enantiomerically enriched beta-aryl-alpha-hydroxy esters. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric Synthesis of Tetrahydroquinolin-3-ols via CoCl₂-Catalyzed Reductive Cyclization of Nitro Cyclic Sulfites with NaBH₄
  作者：Arun R. Jagdale、R. Santhosh Reddy、Arumugam Sudalai

  DOI：10.1021/ol8028109

  日期：2009.2.19

  construction of chiral 3-substituted tetrahydroquinoline derivatives based on asymmetric dihydroxylation and CoCl2-catalyzed reductive cyclization of nitro cyclic sulfites with NaBH4 has been described with high optical purities. This method has been successfully applied in the formal synthesis of PNU 95666E and anachelin H chromophore.

  已经描述了具有高光学纯度的基于不对称二羟基化和CoCl 2催化的硝基环亚硫酸盐与NaBH 4的还原性环化来构建手性3-取代的四氢喹啉衍生物的新方法。该方法已成功地用于PNU 95666E和安那奇林H发色团的形式合成。
• Asymmetric synthesis of l-DOPA and (R)-selegiline via, OsO4-catalyzed asymmetric dihydroxylation
  作者：Iliyas Ali Sayyed、Arumugam Sudalai

  DOI：10.1016/j.tetasy.2004.08.007

  日期：2004.10

  A simple and effective procedure for the enantioselective synthesis of two important neurotransmitter drugs, hat is, (S)-3,4-dihydroxyphenylalanine (L-DOPA) and (R)-N,alpha-dimethyl-N-2-propynylbenzeneethaneamine [(R)-selegiline], is described by employing the Sharpless asymmetric dihydroxylation (AD) as a key step to introduce chirality. (C) 2004 Elsevier Ltd. All rights reserved.