(3aR,7aR)-2,2-dimethylperhydro-1,3-benzodioxol-4-one | 125711-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,7aR)-2,2-dimethylperhydro-1,3-benzodioxol-4-one
• 英文别名: (3aR,7aR)-2,2-dimethyl-hexahydro-2H-1,3-benzodioxol-4-one；(3aR,7aR)-2,2-dimethyl-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-4-one
• CAS: 125711-86-6
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: MRTKVCOALNIMRT-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (3aR,7aR)-2,2-dimethylperhydro-1,3-benzodioxol-4-one 在 偶氮二异丁腈 、 Cp₂TiCl 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.66h， 生成 4-deoxy-1,2-O-isopropylidene-5-S-thio-β-galactosyl-3-S-thio-β-galactosyl-L arabinopyranose
  参考文献：
  名称：

  糖模拟物的硫点击方法

  摘要：

  摘要 将硫并入所需的硫键以进行进一步功能化可通过两种方法获得，这些方法显然是从可用工具池中出现的，特别是硫醇迈克尔烯酮加成 (TMEA) 和硫醇-烯偶联 (TEC)。这两种方法都是高度立体选择性的，并且以总体高产率形成加合物。TEC 硫醇-烯偶联方案用于 ene 2 与 1-硫代葡萄糖和 1-硫代半乳糖的立体选择性和高产率偶联（78% 和 86%） 图形摘要

  DOI：

  10.1080/10426507.2012.736895
• 作为产物：
  描述：

  (3aR,4R,7aR)-2,2-Dimethyl-hexahydro-benzo[1,3]dioxol-4-ol 在 重铬酸吡啶 、 amberlyst-15 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 (3aR,7aR)-2,2-dimethylperhydro-1,3-benzodioxol-4-one
  参考文献：
  名称：

  酶法合成1,2,3-环己三醇的手性异亚丙基衍生物

  摘要：

  2,3-O-异亚丙基-1-环己醇手性结构单元的制备是通过酶解其外消旋的乙酸酯或丁酸正丁酯而获得的高对映体纯度。

  DOI：

  10.1016/s0040-4039(00)99201-3

文献信息

• Intramolecular Chromium(II)-Catalyzed Pinacol Cross Coupling of 2-Methylene-α,ω-dicarbonyls
  作者：Ulrich Groth、Marc Jung、Till Vogel

  DOI：10.1055/s-2004-822895

  日期：——

  Using only 10% of CrCl2 as catalyst, manganese-powder as reducing agent and TMSCl as scavenger, 2-methylene-α,ω-di­aldehydes and -ketones can be coupled to form cyclic diols dia­stereoselectively. The diastereomeric excess strongly depends on the ring size and the substituents of the ω-carbonyl group. The greater the ring size the higher diastereoselectivities are observed. In all cases cis-diols are preferentially formed.

  仅使用CrCl2的10%作为催化剂、锰粉作为还原剂和TMSCl作为清除剂，2-亚甲基-α,ω-二醛和二酮可以立体选择性地耦合形成环状二醇。立体异构过量强烈依赖于环的大小和ω-羰基的取代基。环越大，观察到的立体选择性越高。在所有情况下，优先形成顺式二醇。
• Stereoselective Total Synthesis of (-)-Ovalicin
  作者：J. Yadav、P. Reddy、B. Reddy

  DOI：10.1055/s-0029-1219191

  日期：2010.2

  are ring-closing metathesis, Rubottom oxidation and Corey―Chaykovsky epoxidation. The subsequent transformations are carried out according to Barton's strategy to complete the total synthesis of (―)-ovalicin.

  描述了环氧酮 3 的新合成路线，它是 Barton 从市售 D-核糖合成卵磷脂 (1) 的关键中间体，卵磷脂 (1) 是一种强大的抗血管生成抑制剂。该合成中涉及的关键反应是闭环复分解、Rubottom 氧化和 Corey-Chaykovsky 环氧化。随后的转化按照Barton的策略进行，完成(-)-卵磷脂的全合成。
• Conformationally constrained analogues of 2-arachidonoylglycerol
  作者：Subramanian K. Vadivel、Sundararaman Vardarajan、Richard I. Duclos、JodiAnne T. Wood、Jianxin Guo、Alexandros Makriyannis

  DOI：10.1016/j.bmcl.2007.07.064

  日期：2007.11

  Novel monocyclic analogues of 2-arachidonoylglycerol (2-AG) were designed in order to explore the pharillacophoric conformations of this endocannabinoid ligand at the key cannabinergic proteins. All 2-arachidonoyl esters of 1,2,3-cyclohexanetriol [meso-7 (AM5504), ()+/- 8 (AM5503), and ineso-9 (AM5505)] were synthesized by regioselective acylation of 2,3-dihydroxycyclohexanone followed by selective reductions. The optically active isomers (+)-8 (AM4434) and (-)-8 (AM4435) were synthesized from (2S,3S)- and (2R,3R)-2,3-dihydroxycyclohexanone, respectively, via a chernoenzymatic route. These head group constrained and conformationally restricted analogues of 2-AG as well as the 1-keto precursors were evaluated as substrates for the endocannabinoid deactivating hydrolytic enzymes monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), and also were tested for their affinities for CBI and CB2 cannabinoid receptors. The observed biochemical differences between these ligands can help define the conformational requirements for 2-AG activity at each of the above endocannabinoid protein targets. (c) 2007 Elsevier Ltd. All rights reserved.
• α-Functionalised ketones as promoters of alkene epoxidation by Oxone®
  作者：Alan Armstrong、Barry R. Hayter

  DOI：10.1016/s0040-4020(99)00616-x

  日期：1999.9

  Acceleration of Oxone(R) epoxidation of alkenes by several a-functionalised ketones, including alpha-amido ketones, is investigated. In general, competing decomposition by Baeyer-Villiger reaction prevents use of the ketones as efficient epoxidation promoters. However, a novel oxazolidinone-derived ketone provides epoxides with moderate enantioselectivity (up to 34% ee). (C) 1999 Elsevier Science Ltd. All rights reserved.
• DUMORTIER, L.;EYCKEN, J. VAN DER;VANDEWALLE, M., TETRAHEDRON LETT., 30,(1989) N4, C. 3201-3204
  作者：DUMORTIER, L.、EYCKEN, J. VAN DER、VANDEWALLE, M.

  DOI：——

  日期：——