4-((1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yloxy)-3,5-dimethoxybenzoic acid | 1290633-24-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4-((1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yloxy)-3,5-dimethoxybenzoic acid
• 英文别名: (7S,8S)-4-hydroxy-3,3′,5′-trimethoxy- 8,9-dinor-8,4′-oxyneoligna-7,9-diol-7′-oic acid；(+)-(7S,8S)-4-hydroxy-3,3',5'-trimethoxy-7',8',9'-trinor-8,4'-oxyneolignan-7,9-diol-7'-oic acid；(+)-(7S,8S)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneolignan-7,9-diol-7'-oic acid；4-[(1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxybenzoic acid
• CAS: 1290633-24-7
• 化学式: C₁₉H₂₂O₉
• 分子量: 394.378
• InChiKey: MQVYKIDHPDISFD-IRXDYDNUSA-N

物化性质

• 沸点：
  675.3±55.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-((1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yloxy)-3,5-dimethoxybenzoic acid 、 碘甲烷 在 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以1.3 mg的产率得到methyl 4-((1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yloxy)-3,5-dimethoxybenzoate
  参考文献：
  名称：

  Lignans and Neolignans from Sinocalamus affinis and Their Absolute Configurations

  摘要：

  Twenty-two new lignans and neolignans (1-22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and egthro aryl glycerol units in different neolignans and the CD data [particularly the Rh-2(OCOCF3)(4)-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 mu M, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 +/- 5.9% and 71.7 +/- 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 +/- 2.8% to 91.6 +/- 6.4%, 107.2 +/- 8.0%, and 97.6 +/- 8.5%, respectively.

  DOI：

  10.1021/np200117y
• 作为产物：
  描述：

  丁香酸甲酯 在 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 lithium hydroxide monohydrate 、 palladium on activated charcoal 、 氢气 、 四氯化钛 、 potassium carbonate 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， -78.0~20.0 ℃ 、506.66 kPa 条件下， 反应 41.0h， 生成 4-((1S,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yloxy)-3,5-dimethoxybenzoic acid
  参考文献：
  名称：

  嘧啶酮基手性助剂在醛醇缩合和烷基化反应中的立体调节：氧化炔属的便捷途径。

  摘要：

  （小号）-4-异丙基-1- phenyltetrahydropyrimidin-2（1 ħ） -酮的合成和评价为手性助剂为不对称乙酸酯和丙羟醛缩合反应，通过产生钛和锂烯醇化物，得到用于优异的产率和立体选择性合成和抗醛醇非对映异构体。在锂介导的烷基化反应中也获得了高的立体选择性。辅助助剂的应用在天然氧新木聚糖，（+）-（7 S，8 S）-4-羟基-3,3'，5'-三甲氧基-8'，9'-dinor-的不对称合成中得到了例证8,4'-氧新萘-7,9-二醇-7'-油酸。

  DOI：

  10.1021/ol302653g

文献信息

• Stereoregulations of Pyrimidinone Based Chiral Auxiliary in Aldol and Alkylation Reactions: A Convenient Route to Oxyneolignans
  作者：Mangilal Chouhan、Ratnesh Sharma、Vipin A. Nair

  DOI：10.1021/ol302653g

  日期：2012.11.16

  a chiral auxiliary for asymmetric acetate and propionate aldol reactions, by generation of titanium and lithium enolates, affording excellent yields and stereoselectivities for syn and anti aldol diastereomers, respectively. High stereoselectivities were also obtained in lithium mediated alkylation reactions. The application of the auxiliary was exemplified in the asymmetric synthesis of a natural

  （小号）-4-异丙基-1- phenyltetrahydropyrimidin-2（1 ħ） -酮的合成和评价为手性助剂为不对称乙酸酯和丙羟醛缩合反应，通过产生钛和锂烯醇化物，得到用于优异的产率和立体选择性合成和抗醛醇非对映异构体。在锂介导的烷基化反应中也获得了高的立体选择性。辅助助剂的应用在天然氧新木聚糖，（+）-（7 S，8 S）-4-羟基-3,3'，5'-三甲氧基-8'，9'-dinor-的不对称合成中得到了例证8,4'-氧新萘-7,9-二醇-7'-油酸。
• Lignans and Neolignans from <i>Sinocalamus affinis</i> and Their Absolute Configurations
  作者：Liang Xiong、Chenggeng Zhu、Yanru Li、Ye Tian、Sheng Lin、Shaopeng Yuan、Jinfeng Hu、Qi Hou、Naihong Chen、Yongchun Yang、Jiangong Shi

  DOI：10.1021/np200117y

  日期：2011.5.27

  Twenty-two new lignans and neolignans (1-22), together with 14 known analogues, have been isolated from an ethanolic extract of the stem (with skin removed) of Sinocalamus affinis. Their structures were elucidated by spectroscopic and chemical methods. On the basis of systematic NMR and circular dichroism (CD) data analysis, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and egthro aryl glycerol units in different neolignans and the CD data [particularly the Rh-2(OCOCF3)(4)-induced CD data (the E band)] to determine the absolute configurations at C-8 (C-7) of the aryl glycerol units are discussed. At a concentration of 10 mu M, compounds 20 and 22 inhibited NO production in mouse peritoneal macrophages 84.2 +/- 5.9% and 71.7 +/- 1.0%, respectively. Compounds 19, 20, and 22 showed activity against serum deprivation induced PC12 cell damage by increasing the cell viability from 80.7 +/- 2.8% to 91.6 +/- 6.4%, 107.2 +/- 8.0%, and 97.6 +/- 8.5%, respectively.