(4aS,8aS)-1,4,4a,5,8,8a-Hexahydro-3H-2-benzopyran-3-one | 108098-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (4aS,8aS)-1,4,4a,5,8,8a-Hexahydro-3H-2-benzopyran-3-one
• 英文别名: (4aS,8aS)-hexahydro-3H-2-benzopyran-3-one；(4aS,8aS)-1,4,4a,5,8,8a-hexahydroisochromen-3-one
• CAS: 108098-51-7
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: QMMQQAYCMXPWAC-JGVFFNPUSA-N

物化性质

• 沸点：
  290.8±40.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aS,8aS)-1,4,4a,5,8,8a-Hexahydro-3H-2-benzopyran-3-one 生成 (+/-)-alloyahimbane
  参考文献：
  名称：

  吲哚生物碱。化学酶法对（–）-铝环戊烷的对映选择性合成

  摘要：

  的亲- （[R ）的猪肝酯酶催化的水解的对映特异性内消旋-二乙酸根（2），得到（3）使在天然的higly有效的对映选择性合成中使用的该Chiron公司（ - ） - alloyohimbane（1）。

  DOI：

  10.1039/c39870000299
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 lithium aluminium tetrahydride 、 porcine pancreatic lipase Sigma type 2 作用下， 以 四氢呋喃 为溶剂， 反应 125.17h， 生成 (4aS,8aS)-1,4,4a,5,8,8a-Hexahydro-3H-2-benzopyran-3-one
  参考文献：
  名称：

  Total Synthesis of (+)-Scholarisine A

  摘要：

  An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.

  DOI：

  10.1021/ja211840k

文献信息

• First Enantioselective Synthesis of (-)-Akagerine by a Chemoenzymic Approach
  作者：Bruno Danieli、Giordano Lesma、Marina Mauro、Giovanni Palmisano、Daniele Passarella

  DOI：10.1021/jo00113a034

  日期：1995.4

  (-)-Akagerine (1) was synthesized in an efficient and stereocontrolled fashion from the readily available (1S,2R)-cyclohexenedimethanol monoacetate 4. Key steps were the cleavage of the C(17)/C(18) bond of 14a and the regio- and stereoselective cyclization of the dialdehyde 16 to give the tetracyclic skeleton of akagerine.

  (-)-赤霉素A₁ (1) 由易于获得的 (1S,2R)-环己二烯二甲醇单乙酸酯 4 通过高效且具有立体控制的方式合成。关键步骤包括 14a 中 C(17)/C(18) 键的裂解，以及 1,5-二甲醛 16 的区域选择性和立体选择性环化，从而形成赤霉素的四环骨架结构。
• First enantiodivergent Baeyer–Villiger oxidation by recombinant whole-Cells expressing two monooxygenases from Brevibacterium
  作者：Marko D Mihovilovic、Florian Rudroff、Bernhard Müller、Peter Stanetty

  DOI：10.1016/s0960-894x(03)00137-9

  日期：2003.4

  Microbial Baeyer-Villiger oxidations of representative mesomeric ketones with recombinant Escherichia coli cells expressing two monooxygenases from Brevibacterium were investigated. The two enzymes displayed enantiodivergent biotransformations on an array of structurally diverse substrates, allowing access to some key lactone intermediates in natural compound synthesis.

  研究了具有代表性的美默生酮的微生物Baeyer-Villiger氧化反应，该细菌表达了两种来自短杆菌的单加氧酶的重组大肠杆菌细胞。这两种酶在一系列结构多样的底物上显示出对映异构的生物转化，从而允许在天然化合物合成中获得一些关键的内酯中间体。
• Total Synthesis of (+)-Scholarisine A
  作者：Gregory L. Adams、Patrick J. Carroll、Amos B. Smith

  DOI：10.1021/ja211840k

  日期：2012.3.7

  An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.
• Family Clustering of Baeyer-Villiger Monooxygenases Based on Protein Sequence and Stereopreference
  作者：Marko D. Mihovilovic、Florian Rudroff、Birgit Grötzl、Peter Kapitan、Radka Snajdrova、Joanna Rydz、Robert Mach

  DOI：10.1002/anie.200462964

  日期：2005.6.6
• Access to the Akuammiline Family of Alkaloids: Total Synthesis of (+)-Scholarisine A
  作者：Gregory L. Adams、Patrick J. Carroll、Amos B. Smith

  DOI：10.1021/ja3111626

  日期：2013.1.9

  The planning and implementation of an enantioselective total synthesis of (+)-scholarisine A is presented. Key tactics employed include a novel cyclization, consisting of a nitrile reduction coupled with concomitant addition of the resultant amine to an epoxide; a modified Fischer indolization; an oxidative lactonization of a diol in the presence of an indole ring; and a late-stage cyclization to complete the caged ring scaffold. The development of a possible "retro-biosynthetic" approach to other members of the akuammiline alkaloid family is also described.