3-(6-Methyl-1,4,8,11-tetraoxa-dispiro[4.1.4.2]tridec-6-yl)-propan-1-ol | 1026628-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(6-Methyl-1,4,8,11-tetraoxa-dispiro[4.1.4.2]tridec-6-yl)-propan-1-ol
• 英文别名: 3-(6-Methyl-1,4,8,11-tetraoxadispiro[4.1.47.25]tridecan-6-yl)propan-1-ol
• CAS: 1026628-33-0
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: XWQQQPIVZZYFMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(6-Methyl-1,4,8,11-tetraoxa-dispiro[4.1.4.2]tridec-6-yl)-propan-1-ol 在 amberlyst-15 potassium tert-butylate 、 sodium hydride 、 碳酸氢钠 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 30.17h， 生成 [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (1R,7aS)-1-hydroxy-7a-methyl-1-prop-1-en-2-yl-3,5,6,7-tetrahydro-2H-indene-4-carboxylate
  参考文献：
  名称：

  A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative

  摘要：

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).

  DOI：

  10.1021/jo00099a002
• 作为产物：
  描述：

  2-烯丙基-2-甲基-1,3-环戊二酮 在 三氟甲磺酸三甲基硅酯 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 反应 28.0h， 生成 3-(6-Methyl-1,4,8,11-tetraoxa-dispiro[4.1.4.2]tridec-6-yl)-propan-1-ol
  参考文献：
  名称：

  A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative

  摘要：

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).

  DOI：

  10.1021/jo00099a002

文献信息

• Synthesis of Racemic and Enantiomerically Pure Acetylenic ω-Keto Esters Derived from 2-Methyl-1,3-cycloalkanediones and 2-Methylcycloalkanones Respectively
  作者：Michel Miesch、Philippe Geoffroy、Marie-Paule Ballet、Sidonie Finck、Eric Marchioni、Christophe Marcic

  DOI：10.1055/s-0029-1217043

  日期：2010.1

  Racemic and enantiomerically pure alkynyl esters tethered, respectively, to 2-methyl-1,3-cycloalkanediones and 2-methyl­cycloalkanones were readily obtained starting from common intermediates, which were available on large scale. alkynyl ester - enantiomer-chain - elongation - trimethylsilylpropyne - Corey-Fuchs reaction

  从常见的中间体开始容易地获得分别连接到2-甲基-1,3-环烷二酮和2-甲基环烷酮的外消旋和对映体纯的炔基酯，这些中间体可以大规模获得。 炔基酯-对映体链-伸长率-三甲基甲硅烷基丙炔-Corey-Fuchs反应
• Synthesis of a Bicyclo[2.2.1]heptane Skeleton with Two Oxy-Functionalized Bridgehead Carbons via the Diels–Alder Reaction
  作者：Kazutada Ikeuchi、Tomonari Sasage、Gen Yamada、Takahiro Suzuki、Keiji Tanino

  DOI：10.1021/acs.orglett.1c03451

  日期：2021.12.3

  We describe a synthetic method for a bicyclo[2.2.1]heptane skeleton with two oxy-functionalized bridgehead carbons. This method involves an intermolecular Diels–Alder reaction using 5,5-disubstituted 1,4-bis(silyloxy)-1,3-cyclopentadienes, the diene structure of which has never been synthesized. Furthermore, the intramolecular Diels–Alder reaction using a diene bearing a dienophile moiety at the C-5

  我们描述了一种具有两个氧官能化桥头碳的双环 [2.2.1] 庚烷骨架的合成方法。该方法涉及使用 5,5-二取代的 1,4-双（甲硅烷氧基）-1,3-环戊二烯的分子间 Diels-Alder 反应，其二烯结构从未被合成。此外，使用在 C-5 位带有亲二烯体部分的二烯的分子内 Diels-Alder 反应可以提供包含双环 [2.2.1] 庚烷骨架的三环碳骨架。新型双环[2.2.1]庚烷衍生物可用作有机合成化学的通用构件。
• A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative
  作者：Tadakatsu Mandai、Yuichi Kaihara、Jiro Tsuji

  DOI：10.1021/jo00099a002

  日期：1994.10

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).