(3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one | 155551-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one
• 英文别名: (3aS,7aS)-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxol-4-one
• CAS: 155551-04-5
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: YDSWYZSMUIRRRC-JGVFFNPUSA-N

物化性质

• 熔点：
  82-83 °C(Solvent: Ethyl acetate; Pentane)
• 沸点：
  262.4±40.0 °C(predicted)
• 密度：
  1.113±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one 在 吡啶 作用下， 反应 48.0h， 生成 (3aS,5R,6R,7aS)-6-((1E,3E)-Hepta-1,3-dienyl)-2,2-dimethyl-5-trityloxymethyl-tetrahydro-benzo[1,3]dioxol-4-one
  参考文献：
  名称：

  Landais, Yannick, Chimia, 1998, vol. 52, # 3, p. 104 - 111

  摘要：

  DOI：
• 作为产物：
  描述：

  (3aS,6S,7aS)-6-hydroxy-2,2-dimethyl-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-4-one 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3aS,7aS)-2,2-dimethyl-7,7a-dihydrobenzo[d][1,3]dioxol-4-(3aH)-one
  参考文献：
  名称：

  Chemical synthesis of optically active cis-cyclohexa-3,5-diene-1,2-diols and their 5-2H-derivatives

  摘要：

  A variety of optically active 3-substituted cis-cyclohexane-3,5-dien-1,2-diol acetonides were readily prepared from chiral 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone through a seven-step reaction in good overall yield. The synthesis also allowed preparation of the acetonide having an H-2-atom at the 5-position. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01014-0

文献信息

• Toluene Dioxygenase-Catalyzed Synthesis and Reactions of <i>cis</i>-Diol Metabolites Derived from 2- and 3-Methoxyphenols
  作者：Derek R. Boyd、Narain D. Sharma、John F. Malone、Peter B. A. McIntyre、Colin McRoberts、Stewart Floyd、Christopher C. R. Allen、Amit Gohil、Simon J. Coles、Peter N. Horton、Paul J. Stevenson

  DOI：10.1021/jo5028968

  日期：2015.4.3

  oxidation levels. The relatively stable cyclohexenone cis-diol metabolite from meta methoxyphenol was isolated, while the corresponding metabolite from ortho methoxyphenol was rapidly bioreduced to a cyclohexanone cis-diol. The chemistry of the 3-methoxycyclohexenone cis-diol product was investigated and elimination, aromatization, hydrogenation, regioselective O-exchange, Stork–Danheiser transposition

  用甲苯双加氧酶作为生物催化剂，从间位和邻位甲氧基苯酚中分离出作为其酮互变异构体的对映体纯的顺式-二氢二醇和顺式-四氢二醇代谢物。尽管这些异构苯酚底物在结构上相似，但发现这些生物转化各自的主要生物产物均具有不同的氧化水平。从间甲氧基苯酚中分离出相对稳定的环己烯酮顺式二醇代谢物，而将邻甲氧基苯酚中的相应代谢物迅速生物还原为环己酮顺式二醇。3-甲氧基环己烯酮顺式的化学-二醇产物进行了研究，并观察到了消除，芳构化，氢化，区域选择性O交换，Stork-Danheiser换位和O-甲基化反应。该技术的一个分支提供了由间甲氧基苯酚进行的两步化学酶法合成，该化学酶是最近报道的手性真菌代谢物。该综合还建立了以前未分配的绝对配置。
• Total synthesis of the Amaryllidaceae alkaloid clivonine
  作者：Helmut Haning、Carles Giró-Mañas、Victoria L. Paddock、Christian G. Bochet、Andrew J. P. White、Gerald Bernardinelli、Inderjit Mann、Wolfang Oppolzer、Alan C. Spivey

  DOI：10.1039/c0ob00895h

  日期：——

  syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactonecarbonyl carbon (C7). The synthesis featuring a Bischler–Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine.

  描述了金缕梅科生物碱clivonine（1）的两种合成方法。两者均使用先前报道的7-芳基氢化茚6作为中间体，但在随后引入成为环B内酯羰基碳（C7）的方法上有所不同。这种转化以Bischler-Napieralski反应为特征的合成构成了天然（+）-clivonine的第一个不对称合成。还报道了化合物（±）-13，（±）-16，（-）- 20和（±）-28的晶体结构。
• Methods for inhibiting muscle atrophy
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：US10668087B2

  公开（公告）日：2020-06-02

  In one aspect, the invention relates to methods for treating muscle atrophy by providing to an animal in need thereof an effective amount of a compound. The compound can modulate the expression levels of multiple mRNA of a muscle atrophy signature. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  一方面，本发明涉及通过向有需要的动物提供有效量的化合物来治疗肌肉萎缩的方法。该化合物可调节肌肉萎缩特征的多种 mRNA 的表达水平。本摘要旨在作为一种扫描工具，用于在特定技术领域进行搜索，并非对本发明的限制。
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
• Suprafaciality of Thermal N-4-Alkenylhydroxylamine Cyclizations: syntheses of (.+-.)-.alpha.-Lycorane and (+)-Trianthine
  作者：Wolfgang Oppolzer、Alan C. Spivey、Christian G. Bochet

  DOI：10.1021/ja00086a060

  日期：1994.4