(7aS)-5,5-ethylenedioxy-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-one | 260048-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7aS)-5,5-ethylenedioxy-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-one
• 英文别名: (7'aS)-7'a-methylspiro[1,3-dioxolane-2,5'-2,3,6,7-tetrahydroindene]-1'-one
• CAS: 260048-45-1
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: IDNGPDCVGAFDKM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (7aS)-5,5-ethylenedioxy-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-one 在 sodium ethanolate 、 magnesium 作用下， 以 乙醇 为溶剂， 生成 methyl 2-((1R,7aR)-7a-methyl-1,2,3,6,7,7a-hexahydrospiro[indene-5,2'-[1,3]dioxolan]-1-yl)acetate
  参考文献：
  名称：

  Hajos二酮中维生素D环C / D结构单元的一种新方法，涉及在更多取代的碳原子上形成环氧化物

  摘要：

  已开发出一种新的方法，用于从Hajos二酮合成1α，25-二羟基维生素D 3（骨化三醇）的反式-氢化茚构件。Hajos二酮中的α，β-不饱和羰基已得到保护，五元环中的羰基已用于侧链连接。六元环转化的关键步骤包括：羰基的还原，烯丙基醇中双键的立体选择性环氧化，在更多取代的碳原子处环氧化物的开放和区域选择性脱氧。

  DOI：

  10.1016/j.tetlet.2006.06.115
• 作为产物：
  描述：

  (S)-(+)-2,3,7,7A-四氢-7A-甲基-1H-茚-1,5(6H)-二酮 、 1,2-bis(trimethylsilyl)ethane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到(7aS)-5,5-ethylenedioxy-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-1-one
  参考文献：
  名称：

  Synthesis and inotropic activity of hydroindene derivatives

  摘要：

  A synthetic approach to hydroindenic inotropic agents has been developed, starting from enantiopure Hajos-Parrish (1), Hajos-Wiechert (2), and related diketones. Their transformation: into C-l formyl derivatives and other subsequent synthetic targets is described. The results of the thermodynamic equilibration between both epimers of each formyl derivative are analysed. The inotropic activities of selected compounds on right and left atrial preparations are also evaluated and discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00251-5

文献信息

• Allyl‐Palladium‐Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β‐Vicinal Difunctionalization
  作者：Yifeng Chen、David Huang、Yizhou Zhao、Timothy R. Newhouse

  DOI：10.1002/anie.201704874

  日期：2017.7.3

  The telescoping of allyl‐palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts. The compatibility of the dehydrogenation conditions additionally allows for efficient

  烯丙基钯催化的酮脱氢与有机铜酸酯共轭加成化学的伸缩作用使芳基，杂芳基，乙烯基，酰基，甲基和其他官能化烷基可通过其对映异构体化学选择性地引入到各种未活化的酮化合物中。脱氢条件的相容性还允许中间烯醇与各种亲电试剂的有效捕集。通过与几个先前报告的多步骤序列进行比较，证明了该方法的实用性。
• Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation
  作者：David Huang、Yizhou Zhao、Timothy R. Newhouse

  DOI：10.1021/acs.orglett.7b03818

  日期：2018.2.2

  The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

  报道了烯丙基钯催化通过酮的烯醇锌对酮进行α，β-脱氢的一步。优化后的协议利用市售的Zn（TMP）2作为碱，并使用磷酸二乙基烯丙酯作为氧化剂。值得注意的是，这种转化是在无盐条件下进行的，并能耐受各种环烷酮。
• Synthesis and inotropic activity of hydroindene derivatives
  作者：Luis G. Sevillano、Concepción P. Melero、Melchor Boya、Jose Luis López、Fernando Tomé、Esther Caballero、Rosalı́a Carrón、M. José Montero、Manuel Medarde、Arturo San Feliciano

  DOI：10.1016/s0968-0896(99)00251-5

  日期：1999.12

  A synthetic approach to hydroindenic inotropic agents has been developed, starting from enantiopure Hajos-Parrish (1), Hajos-Wiechert (2), and related diketones. Their transformation: into C-l formyl derivatives and other subsequent synthetic targets is described. The results of the thermodynamic equilibration between both epimers of each formyl derivative are analysed. The inotropic activities of selected compounds on right and left atrial preparations are also evaluated and discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A new approach to a vitamin D ring C/D building block from the Hajos dione, involving epoxide opening at the more substituted carbon atom
  作者：Paweł Chochrek、Alicja Kurek-Tyrlik、Karol Michalak、Jerzy Wicha

  DOI：10.1016/j.tetlet.2006.06.115

  日期：2006.8

  1α,25-dihydroxyvitamin D3 (calcitriol) synthesis from the Hajos dione has been developed. The α,β-unsaturated carbonyl group in the Hajos dione has been protected and the carbonyl group in the five-membered ring has been used for the side chain attachment. Key steps in the six-membered ring transformation include: reduction of the carbonyl group, stereoselective epoxidation of the double bond in the

  已开发出一种新的方法，用于从Hajos二酮合成1α，25-二羟基维生素D 3（骨化三醇）的反式-氢化茚构件。Hajos二酮中的α，β-不饱和羰基已得到保护，五元环中的羰基已用于侧链连接。六元环转化的关键步骤包括：羰基的还原，烯丙基醇中双键的立体选择性环氧化，在更多取代的碳原子处环氧化物的开放和区域选择性脱氧。