2-(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethanal | 82896-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethanal
• 英文别名: (2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethanal；2-(2,4,10-trioxatricyclo[3.3.1.1^3,7]dec-3-yl)acetaldehyde；2-(2,4,10-Trioxa-adamant-3-yl)-ethanal；(2,4,10-trioxa-adamantan-3-yl)-acetaldehyde；3-Formylmethyl-2,4,10-trioxa-adamantan；2-(2,4,10-Trioxatricyclo[3.3.1.13,7]decan-3-yl)acetaldehyde
• CAS: 82896-24-0
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: INEARFQNCHBPLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethanal 在 Amberlyst 15 、 水 作用下， 以 丙酮 、 苯 为溶剂， 反应 36.0h， 生成 5-Oxo-hex-2-ensaeure-(3,5-dihydroxycyclohexyl)-ester
  参考文献：
  名称：

  Synthese von ?-Acetyl-?-methylenpolyencarbons�ureestern

  摘要：

  The alpha-methylenpolyene carboxylic acids 1 and 2 are highly active against Gram-positive bacteria. If this activity arises from an interference with the cell membranes, then an abrupt change in biological properties is to be expected with growing chain length of simple model compounds. To make these tests possible, we describe here the synthesis of a series of homologue esters of type 40. Their synthesis was achieved by Wittig reactions of polyene alpha,omega-dialdehydes 6 with acetyl-methylentriphenylphosphoran 5a and the protected carboxymethylmethylen triphenylphosphonium salt 8.

  DOI：

  10.1002/prac.19943360806
• 作为产物：
  描述：

  间苯三酚 在 镍 lithium aluminium tetrahydride 、 草酰氯 、 三氟化硼 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 反应 0.5h， 生成 2-(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)ethanal
  参考文献：
  名称：

  Synthese von ?-Acetyl-?-methylenpolyencarbons�ureestern

  摘要：

  The alpha-methylenpolyene carboxylic acids 1 and 2 are highly active against Gram-positive bacteria. If this activity arises from an interference with the cell membranes, then an abrupt change in biological properties is to be expected with growing chain length of simple model compounds. To make these tests possible, we describe here the synthesis of a series of homologue esters of type 40. Their synthesis was achieved by Wittig reactions of polyene alpha,omega-dialdehydes 6 with acetyl-methylentriphenylphosphoran 5a and the protected carboxymethylmethylen triphenylphosphonium salt 8.

  DOI：

  10.1002/prac.19943360806

文献信息

• A Total Synthesis of Xestodecalactone A and Proof of Its Absolute Stereochemistry:  Interesting Observations on Dienophilic Control with 1,3-Disubstituted Nonequivalent Allenes
  作者：Toshiharu Yoshino、Fay Ng、Samuel J. Danishefsky

  DOI：10.1021/ja064270e

  日期：2006.11.1

  A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered.

  描述了使用 Diels-Alder 策略的 xestodecalactone A 的简明全合成。焦点 Diels-Alder 反应依赖于“ynoate”亲二烯体来快速组装所需的间苯二甲酸支架。在这项研究中，研究了涉及 1,3-二取代的非等价丙二烯亲二烯体的 Diels-Alder 环加成反应，并遇到了一些令人惊讶的结果。
• Electrochemical C−H/N−H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles
  作者：Zhong‐Wei Hou、Zhong‐Yi Mao、Huai‐Bo Zhao、Yared Yohannes Melcamu、Xin Lu、Jinshuai Song、Hai‐Chao Xu

  DOI：10.1002/anie.201602616

  日期：2016.8

  their prevalence in nature and their broad utility in pharmaceutical industry. Reported herein is an unprecedented noble‐metal‐ and oxidant‐free electrochemical method for the coupling of (hetero)arylamines with tethered alkynes to synthesize highly functionalized indoles, as well as the more challenging azaindoles.

  吲哚和氮杂吲哚由于其在自然界中的普遍性及其在制药工业中的广泛应用而成为最重要的杂环。本文报道了一种前所未有的无贵金属，无氧化剂的电化学方法，用于将（杂）芳基胺与链状炔烃偶联，以合成高度官能化的吲哚以及更具挑战性的氮吲哚。
• Nowak, Wolfgang; Gerlach, Hans, Liebigs Annalen der Chemie, 1993, # 2, p. 153 - 160
  作者：Nowak, Wolfgang、Gerlach, Hans

  DOI：——

  日期：——
• Syntheses de (R,S) mevalonolactones marquees au 14C ou au 13C : (R,S) mevalonolactone (14C-4,5) ; (14C-5) ; (14C-3′)
  作者：Bernard Rousseau、Jean-Pierre Beaucourt、Louis Pichat

  DOI：10.1016/s0040-4039(00)87294-9

  日期：1982.1
• Bauer, Sonja; Spiteller, Gerhard, Liebigs Annalen der Chemie, 1985, # 4, p. 813 - 821
  作者：Bauer, Sonja、Spiteller, Gerhard

  DOI：——

  日期：——