meso-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester | 97116-47-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: meso-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester
• 英文别名: Dimethyl 3,4-bis(4-methoxyphenyl)hexanedioate
• CAS: 97116-47-7
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: IGCAIHLXNHWPFM-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  494.1±45.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  racem-3,4-Bis-(4-methoxy-phenyl)-hexan-1,6-diol 在 盐酸 、 Jones oxidative system 作用下， 以 丙酮 为溶剂， 反应 0.5h， 生成 meso-3,4-Bis-(4-methoxy-phenyl)-adipinsaeure-dimethylester
  参考文献：
  名称：

  Stereoselective Hydrocoupling of [(1R)-exo]-3-exo-(Diphenylmethyl)bornyl Cinnamates by Electroreduction

  摘要：

  [GRAPHICS]The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, synthesized from (1R)-(+)-camphor in three steps, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.

  DOI：

  10.1021/ol016566p

文献信息

• Photoinduced electron transfer reaction of cyclopropanone acetals with arylmethyl methanesulfonate: generation of β-keto radical species and application to C–C bond formation
  作者：Manabu Abe、Akira Oku

  DOI：10.1039/c39940001673

  日期：——

  The photoinduced electron transfer reaction of the cyclopropanone acetals 1 with arylmethyl methanesulfonates 4 or 10 as electron acceptors was found to generate a transient pair of radicals, the β-keto radical 3 and the arylmethyl radical, which underwent a novel carbon–carbon bond formation reaction at the sterically hindered β-position of the esters.

  研究发现，环丙酮缩醛 1 与作为电子受体的芳基甲基甲烷磺酸盐 4 或 10 发生光诱导电子转移反应时，会产生一对瞬时自由基--δ-酮自由基 3 和芳基甲基自由基，这对自由基在酯的立体受阻δ位上发生了新的碳碳键形成反应。
• N-Heterocyclic Carbene Catalyzed Cross Dehydrogenative Coupling of Aldehydes with Methanol: Combined Use of Eosin Y and Hexachloroethane
  作者：Hideto Miyabe、Eito Yoshioka、Hiroki Takahashi、Akane Kubo、Miki Ohno、Fuuka Watanabe、Rino Shiono、Yuuki Miyazaki

  DOI：10.1055/a-1918-4406

  日期：2022.12

  Cross dehydrogenative coupling of aldehydes with methanol was investigated under organocatalytic conditions based on the cooperation­ between N-heterocyclic carbene and eosin Y·Na as an organophotocatalys­t. The combined use of eosin Y·Na and hexachloro­ethane (C2Cl6) was the effective method for the oxidative esterification of various aldehydes, because the oxidation steps are promoted by two pathways

  基于N-杂环卡宾与曙红Y·Na作为有机光催化剂的协同作用，在有机催化条件下研究了醛与甲醇的交叉脱氢偶联。曙红Y·Na和六氯乙烷（C 2 Cl 6）的联合使用是各种醛氧化酯化的有效方法，因为氧化步骤由与活化光催化剂和C 2 Cl 6相关的两条途径促进。相比之下，曙红 Y·Na 和溴三氯甲烷 (BrCCl 3 ) 的联合使用仅对简单的肉桂醛衍生物的氧化酯化有效，其中 BrCCl 3促进作为溴化试剂向自由基中间体的氧化。
• Stereoselective Hydrocoupling of [(1<i>R</i>)-<i>e</i><i>xo</i>]-3-<i>e</i><i>xo</i>-(Diphenylmethyl)bornyl Cinnamates by Electroreduction
  作者：Naoki Kise、Keisuke Iwasaki、Naohiko Tokieda、Nasuo Ueda

  DOI：10.1021/ol016566p

  日期：2001.10.1

  [GRAPHICS]The chiral auxiliary [(1R)-exo]-3-exo-(diphenylmethyl)borneol, synthesized from (1R)-(+)-camphor in three steps, was highly effective for the stereoselective hydrocoupling of its cinnamates by electroreduction. From the resulting hydrodimers, (3R,4R)-3,4-diaryladipic acid esters and (3R,4R)-3,4-diarylhexane-1,6-diols were synthesized in 87-95% ee.