4-benzyloxy-3-methoxybenzaldehyde-bis-phenylthioacetal | 123195-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-benzyloxy-3-methoxybenzaldehyde-bis-phenylthioacetal
• 英文别名: 4-[Bis(phenylsulfanyl)methyl]-2-methoxy-1-phenylmethoxybenzene
• CAS: 123195-63-1
• 化学式: C₂₇H₂₄O₂S₂
• 分子量: 444.618
• InChiKey: VMNNJZCZYGWKDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-3-methoxybenzaldehyde-bis-phenylthioacetal 在 sodium tetrahydroborate 、 正丁基锂 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 9.5h， 生成 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone
  参考文献：
  名称：

  Brinksma, Jelle; Van Der Deen, Hanneke; Van Oeveren, Arjan, Journal of the Chemical Society. Perkin transactions I, 1998, # 24, p. 4159 - 4163

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醛 、 苯硫酚 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到4-benzyloxy-3-methoxybenzaldehyde-bis-phenylthioacetal
  参考文献：
  名称：

  Brinksma, Jelle; Van Der Deen, Hanneke; Van Oeveren, Arjan, Journal of the Chemical Society. Perkin transactions I, 1998, # 24, p. 4159 - 4163

  摘要：

  DOI：

文献信息

• Pinoresinol‐lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties
  作者：Julianne K. Hwang、Syed G.A. Moinuddin、Laurence B. Davin、Norman G. Lewis

  DOI：10.1002/chir.23218

  日期：2020.6

  Two western red cedar pinoresinol‐lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8‐ and 8′‐linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can

  研究了两个西部红柏松脂松香醇-larresresinol还原酶（PLR）的同系物，以确定它们的对映选择性，底物通用性和动力学性质。PLR位于产生的稀疏蛋白质，针叶树醇衍生的立体选择性偶联的下游，以使其进入8和8'连接的呋喃呋喃木脂体木脂松酚。我们的研究表明，每个PLR同源物都可以通过修饰的芳环取代基对映异构地代谢不同的呋喃呋喃木脂素，但是其中C4 / C4'上的酚基对于催化是必不可少的。这些结果与PLR活性部位中醌甲基化物中间体的形成是一致的。定点诱变和动力学测量提供了对影响对映选择性和动力学性质的因素的进一步了解。根据这些数据，
• General conjugate-addition method for the synthesis of enantiomerically pure lignans. Total synthesis of (-)- and (+)-burseran, (-)-dehydroxycubebin, (-)-trichostin, (-)-cubebin, (-)-5''-methoxyhinokinin, and (-)-hinokinin
  作者：Nicola Rehnberg、Goeran Magnusson

  DOI：10.1021/jo00301a026

  日期：1990.7
• Formation of (−)-arctigenin in Forsythia intermedia
  作者：Shuji Ozawa、Laurence B. Davin、Norman G. Lewis

  DOI：10.1016/s0031-9422(00)95149-5

  日期：1993.2

  Forsythia intermedia cell-free extracts were examined for their ability to catalyse the enantioselective and regiospecific O-methylation of matairesinol. In contrast to the enzymatic steps defined from (+)-pinoresinol to (-)-matairesinol, the conversion of matairesinol into arctigenin was not highly enantioselective; both (+)- and (-)- antipodes of matairesinol served as substrates for methylation, with the naturally occurring (-)-enantiomer slightly preferred. But the cell-free extracts also catalysed the synthesis of (+)- and (-)-isoarctigenins, with (-)-matairesinol again the preferred substrate. Thus the O-methylation of matairesinol, catalysed by F. intermedia cell-free extracts, is neither highly enantioselective nor regiospecific. No evidence that subsequent methylation of either arctigenin or isoarctigenin occurred to afford dimethyl matairesinol was obtained, i.e. the O-methyltransferase(s) only catalysed monomethylation. Taken together, it is proposed that post-coupling methylation does not proceed via regiospecific methylation of matairesinol to give arctigenin directly. Instead, regiospecific glucosylation first occurs to afford matairesinoside; subsequent methylation affords arctiin, which is then converted into arctigenin via action of a beta-glucosidase.
• Synthesis of enterolactone and enterodiol precursors as potential inhibitors of human estrogen synthetase (aromatase)
  作者：T Mäkelä

  DOI：10.1016/s0039-128x(00)00104-5

  日期：2000.8

  A series of variably substituted derivatives of lignan lactones and diols were prepared using tandem conjugate addition reaction as a key step. These theoretical precursors of the mammalian lignans enterolactone 1 and enterodiol 3 are moderate or weak inhibitors of human aromatase activity. (C) 2000 Elsevier Science Inc. All rights reserved.
• Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum
  作者：Zhi-Qiang Xia、Michael A Costa、John Proctor、Laurence B Davin、Norman G Lewis

  DOI：10.1016/s0031-9422(00)00242-9

  日期：2000.11

  Given the importance of the antitumor/antiviral lignans, podophyllotoxin and 5-methoxypodophyllotoxin, as biotechnological targets, their biosynthetic pathways were investigated in Podophyllum peltatum and Linum flavum. Entry into their pathways was established to occur via dirigent mediated coupling of E-coniferyl alcohol to afford (+)-pinoresinol; the encoding gene was cloned and the recombinant protein subsequently obtained. Radiolabeled substrate studies using partially purified enzyme preparations next revealed (+)-pinoresinol was enantiospecifically converted sequentially into (+)-lariciresinol and (-)-secoisolariciresinol via the action of an NADPH-dependent bifunctional pinoresinol/lariciresinol reductase. The resulting (-)-secoisolariciresinol was enantiospecifically dehydrogenated into (-)-matairesinol, as evidenced through the conversion of both radio- and stable isotopically labeled secoisolariciresinol into matairesinol, this being catalyzed by the NAD-dependent secoisolariciresinol dehydrogenase. (-)-Matairesinol was further hydroxylated to afford 7'-hydroxymatairesinol, this being efficiently metabolized into 5-methoxypodophyllotoxin. Thus much of the overall biosynthetic pathway to podophyllotoxin has been established, that is, from the dirigent mediated coupling of E-coniferyl alcohol to the subsequent conversions leading to 7'-hydroxymatairesinol. (C) 2000 Elsevier Science Ltd. All rights reserved.