dimethyl 3-[(4aR,6aS,10aS,10bR)-3-(methoxycarbonyl)-4a,7,7,10a-tetramethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f ]chromen-2-yl]pyridine-2,6-dicarboxylate | 890026-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: dimethyl 3-[(4aR,6aS,10aS,10bR)-3-(methoxycarbonyl)-4a,7,7,10a-tetramethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f ]chromen-2-yl]pyridine-2,6-dicarboxylate
• 英文别名: dimethyl 3-[(4aR,6aS,10aS,10bR)-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-2-yl]-2,6-pyridinedicarboxylate；thallusin trimethyl ester；dimethyl 3-[(4aR,6aS,10aS,10bR)-3-methoxycarbonyl-4a,7,7,10a-tetramethyl-1,5,6,6a,8,9,10,10b-octahydrobenzo[f]chromen-2-yl]pyridine-2,6-dicarboxylate
• CAS: 890026-21-8
• 化学式: C₂₈H₃₇NO₇
• 分子量: 499.604
• InChiKey: ZWLCEQVNIKTNIG-RTPQPHRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl 3-[(4aR,6aS,10aS,10bR)-3-(methoxycarbonyl)-4a,7,7,10a-tetramethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f ]chromen-2-yl]pyridine-2,6-dicarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以91%的产率得到3-[(4aR,6aS,10aS,10bR)-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-3-(hydroxymethyl)-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-2-yl]-2,6-pyridinedimethanol
  参考文献：
  名称：

  Synthesis of ent-Thallusin

  摘要：

  three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(l) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.

  DOI：

  10.1021/ol0605777
• 作为产物：
  描述：

  [4aR-(4aα,6aβ,10aα,10bβ)]-2-bromo-3-(bromomethyl)-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran 在 四(三苯基膦)钯 sodium chlorite 、 sodium dihydrogenphosphate 、 copper(l) iodide 、 2,3-二甲基-2-丁烯 、 溴 、 potassium carbonate 、 calcium carbonate 作用下， 以 甲醇 、 乙醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 9.5h， 生成 dimethyl 3-[(4aR,6aS,10aS,10bR)-3-(methoxycarbonyl)-4a,7,7,10a-tetramethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f ]chromen-2-yl]pyridine-2,6-dicarboxylate
  参考文献：
  名称：

  Synthesis of ent-Thallusin

  摘要：

  three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(l) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.

  DOI：

  10.1021/ol0605777

文献信息

• Total Synthesis of (−)-Thallusin: Utilization of Enzymatic Hydrolysis Resolution
  作者：Hirofumi Yamamoto、Yuichi Takagi、Takaki Oshiro、Tadashi Mitsuyama、Ikuo Sasaki、Naoto Yamasaki、Akiyo Yamada、Hiromichi Kenmoku、Yoshihide Matsuo、Yusuke Kasai、Hiroshi Imagawa

  DOI：10.1021/jo501720b

  日期：2014.9.19

  (−)-Thallusin, isolated from a marine bacterium, is the only known natural product to act as an algal morphogenesis inducer. Because (−)-thallusin can only be obtained in exceedingly limited amounts from microbial cultivation, a synthetic supply of this compound is highly desirable. Here, we describe a novel synthetic pathway to (±)-thallusin and the first asymmetric synthesis of (−)-thallusin utilizing

  从海洋细菌中分离出来的（-）-hallusin是唯一已知的可充当藻类形态发生诱导剂的天然产物。由于从微生物培养中只能以非常有限的量获得（-）-牛柳素，因此非常需要合成供应该化合物。在这里，我们描述了一种新的合成途径，以（±）-蛋黄素和脂酶PS-30和脂酶M Amamo-10的组合，利用酶促水解拆分合成了（-）-蛋黄素。
• US7279314B2
  申请人：——

  公开号：US7279314B2

  公开（公告）日：2007-10-09
• Synthesis of <i>e</i><i>nt</i>-Thallusin
  作者：Xiaolei Gao、Yoshihide Matsuo、Barry B. Snider

  DOI：10.1021/ol0605777

  日期：2006.5.1

  three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(l) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.