8-(2-hydroxyethyl)-1,4-dioxaspiro[4,5]decan-8-ol | 189509-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(2-hydroxyethyl)-1,4-dioxaspiro[4,5]decan-8-ol
• 英文别名: 8-Hydroxy-1,4-dioxaspiro[4.5]decane-8-ethanol；8-(2-hydroxyethyl)-1,4-dioxaspiro[4.5]decan-8-ol
• CAS: 189509-23-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: JRVGHLJGDMBZCR-UHFFFAOYSA-N

物化性质

• 沸点：
  347.9±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(2-hydroxyethyl)-1,4-dioxaspiro[4,5]decan-8-ol 在 吡啶 、 甲醇 、 Dowex 50X₈-100 (H⁺ form) 、 Sulfolobus solfataricus crude homogenate 、 水 、 potassium carbonate 、 lithium tri-sec-butyl(hydrido)borate 作用下， 以 四氢呋喃 为溶剂， 反应 66.0h， 生成 isorengyoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of rengyoside -A, -B, isorengyoside and synthesis of their aglycones

  摘要：

  The chemoenzymatic synthesis of a group of naturally occurring cyclohexylethanoids, rengyoside-A, -B and isorengyoside, has been performed by enzymatic glucosidation of their chemically synthesized aglycones, rengyol, rengyoxide and isorengyol. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00138-5
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 lithium aluminium tetrahydride 、 锌 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 8-(2-hydroxyethyl)-1,4-dioxaspiro[4,5]decan-8-ol
  参考文献：
  名称：

  氧催化的双环醚的立体选择性合成的碘催化的无金属多米诺方法†

  摘要：

  已经开发了一种多米诺反应，通过在25℃的二氯甲烷中存在10 mol％的分子碘的情况下，通过将4-（2-羟乙基）环己-3-烯醇与醛偶联来合成氧桥联的双环醚。该方法是高度非对映选择性的，以高收率和高选择性提供了相应的双环醚，即八氢-4a，7-环氧异色酮。这是有关使用多米诺普林斯策略合成氧桥联双环醚的第一份报告。

  DOI：

  10.1039/c5ob00518c

文献信息

• A new approach to the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans by the 1,5-CH insertion reaction of magnesium carbenoids
  作者：Tsuyoshi Satoh、Tsukasa Yasoshima、Hitoshi Momochi

  DOI：10.1016/j.tetlet.2012.02.034

  日期：2012.4

  in high to quantitative yields via the 1,5-CH insertion reaction of generated magnesium carbenoid intermediates. When this procedure was commenced with acyclic ketones, multi-substituted tetrahydrofurans were obtained in up to a 96% yield. This procedure provides a new and good way for the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans with the formation of a carbon–carbon bond between a carbenoid

  由各种环状酮以良好的总收率制备了1-烷氧基-1- [2-氯-2-（对甲苯基亚磺酰基）乙基]环烷烃。用i处理这些带有亚硫酰基的环烷烃-PrMgCl通过生成的镁类马鞭草中间体的1，5-CH插入反应，以高至定量的产率形成了1-oxaspiro [4.n]烷烃。当从无环酮开始该程序时，以高达96％的收率获得了多取代的四氢呋喃。该方法为合成1-oxaspiro [4.n]烷烃和四氢呋喃提供了一种新的良好方法，该方法可以高产率地在类胡萝卜素碳和非活性碳之间形成碳-碳键。事实证明，镁类胡萝卜素中间体中的氧原子在1,5-CH插入反应中起着非常重要的作用。
• Intramolecular Heck cyclization to the galanthamine-type alkaloids: total synthesis of (±)-lycoramine
  作者：Pi-Hui Liang、Jing-Ping Liu、Ling-Wei Hsin、Chen-Yu Cheng

  DOI：10.1016/j.tet.2004.09.044

  日期：2004.12

  A novel approach towards the construction of the galanthamine skeleton was demonstrated by the total synthesis of (±)-lycoramine. The key steps include a Pd-catalyzed intramolecular cyclization to form the seven-membered azepane ring and a spontaneous intramolecular Michael addition to afford the five-membered furan ring. This synthetic route has also been demonstrated to be useful for the preparation

  （±）-lycoramine的全合成证明了一种构造加兰他敏骨架的新颖方法。关键步骤包括钯催化的分子内环化反应以形成七元氮杂环戊烷环和自发的分子内迈克尔加成反应以提供五元呋喃环。该合成途径也已被证明可用于制备具有简化的加兰他敏骨架的新型衍生物。
• Synthesis of Galanthamine Analogs as Acetylcholinesterase Inhibitors via Intramolecular Heck Cyclization
  作者：Pi-Hui Liang、Ling-Wei Hsin、Sung-Ling Pong、Chia-Huei Hsu、Chen-Yu Cheng

  DOI：10.1002/jccs.200300071

  日期：2003.6

  A novel approach towards the construction of the galanthamine skeleton was demonstrated by the Pd-catalyzed cyclization of N-[2-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-ethyl]-2-iodo-4-methoxy-N-methyl-benzamide (23), with formation of the benzazepine ring and creation of a quaternary carbon.

  N-[2-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-ethyl] 的 Pd 催化环化证明了一种构建加兰他敏骨架的新方法-2-iodo-4-methoxy-N-methyl-benzamide (23)，形成苯并氮杂环并产生季碳。
• Grob-Type Fragmentation Releases Paracyclophane Ring Strain in a Late-Stage Precursor of Haouamine A
  作者：Liming Cao、Chenbo Wang、Peter Wipf

  DOI：10.1021/acs.orglett.9b00424

  日期：2019.3.1

  A ketene [2 + 2]-addition, an intramolecular aldol reaction, a Suzuki–Miyaura coupling, and a chemoselective lactam reduction were used to prepare a late-stage precursor of haouamine A. Exposure to acid led to a Grob-type fragmentation of the strained 3-aza[7]paracyclophane ring, followed by a tandem Pictet–Spengler reaction of the intermediate iminium ion and conversion to a novel 1,4a-propanocyclopenta[b]pyridine

  烯酮[2 + 2]加成，分子内醛醇缩合反应，Suzuki-Miyaura偶联和化学选择性内酰胺还原被用于制备花甲胺A的后期前体。暴露于酸中会导致Grob型碎裂应变后的3-氮杂[7]对环环烷环，随后是中间亚胺离子的串联Pictet-Spengler反应，并转化为新型的1,4a-丙环戊[ b ]吡啶。该级联反应也可能与天然产物的作用机理有关。
• Synthesis of 13C-Labeled Possible Intermediates in the Biosynthesis of Phenylethanoid Derivatives, Cornoside and Rengyosides.
  作者：Hiroshi KUWAJIMA、Yoshitaka TAKAI、Kiyokazu TAKAISHI、Kenichiro INOUE

  DOI：10.1248/cpb.46.581

  日期：——

  In order to clarify the biosynthetic pathway of C6-C2 unit compounds containing salidroside, cornoside, and rengyosides A and B in oleaceous plants, 13C-labeled putative precursors, 4-hydroxyphenylethanol, salidroside and cornoside, were prepared.

  为了弄清油料植物中含有水杨苷、玉米须苷、雷公藤苷 A 和 B 的 C6-C2 单元化合物的生物合成途径，制备了 13C 标记的假定前体--4-羟基苯乙醇、水杨苷和玉米须苷。