(R)-1-(furan-3-yl)but-3-en-1-ol | 144635-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (R)-1-(furan-3-yl)but-3-en-1-ol
• 英文别名: (R)-1-(3-furyl)-3-buten-1-ol；(R)-1-(3-furyl)but-3-en-1-ol；1-(3-furyl)-3-buten-1-ol；r-1-(3-Furyl)-3-buten-1-ol；(1R)-1-(furan-3-yl)but-3-en-1-ol
• CAS: 144635-05-2
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: YFOVGIPVIZYMST-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(furan-3-yl)but-3-en-1-ol 在 Grubbs catalyst first generation 乙烯 、 sodium hydride 作用下， 以 二氯甲烷 、 苯 为溶剂， 5.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (+)-2-(furan-3-yl)-5-vinyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Total Syntheses of (+)- and (−)-Cacospongionolide B, Cacospongionolide E, and Related Analogues. Preliminary Study of Structural Features Required for Phospholipase A₂ Inhibition

  摘要：

  The total syntheses of the antiinflammatory marine sponge metabolites (+)-cacospongionolide B and E are described. The pivotal steps in the synthetic route include a three-step sequence that couples the two main regions of the natural product, as well as generates the side chain dihydropyran ring. The activity of the synthetic analogues against bee venom phospholipase A(2) suggests that the cacospongionolides have enantiospecific interactions with the enzyme that may be independent of the gamma-hydroxybutenolide moiety.

  DOI：

  10.1021/jo049285e
• 作为产物：
  描述：

  3-糠醛 在 pseudomonas fluorescens lipase 、 氯化铵 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 phosphate buffer 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 72.0h， 生成 (R)-1-(furan-3-yl)but-3-en-1-ol
  参考文献：
  名称：

  1-（3-呋喃基）-3-丁烯-1-醇的酶动力学拆分

  摘要：

  通过相应乙酸盐的对映选择性水解研究了1-（3-呋喃基）-3-丁烯-1-醇的酶促动力学拆分。荧光假单胞菌（Fluka）被发现在所筛选的11种脂肪酶中具有最高的对映体比率。转化率为51％时，发现该产品的ee值（ee p）为89％，对映体比率（E p）为58，而底物的ee值（ee s）为89％，得到一个对映体比率（E p）为38。

  DOI：

  10.1016/j.tetasy.2005.06.013

文献信息

• Proline-Based <i>N</i>-Oxides as Readily Available and Modular Chiral Catalysts. Enantioselective Reactions of Allyltrichlorosilane with Aldehydes
  作者：John F. Traverse、Yu Zhao、Amir H. Hoveyda、Marc L. Snapper

  DOI：10.1021/ol050814q

  日期：2005.7.1

  as an effective catalyst for the reaction of allyltrichlorosilane with aryl and alpha,beta-unsaturated aldehydes at room temperature to afford the desired homoallylic alcohols in up to 92% ee. The chiral catalyst can be easily prepared from optically pure proline in three simple steps and 60% overall yield.

  [反应：请参见文字]。鉴定出基于脯氨酸的N-氧化物，其可作为烯丙基三氯硅烷与芳基和α，β-不饱和醛在室温下反应的有效催化剂，以提供高达92％ee的所需均烯丙基醇。可以通过三个简单的步骤由旋光纯的脯氨酸轻松制备手性催化剂，且总收率为60％。
• Synthetic Study on Clutiolide Based on a Remote Chelation Controlled Ireland-Claisen Rearrangement
  作者：Susumi Hatakeyama、Jun Ishihara、Okihisa Tokuda、Kazunori Shiraishi、Yukihiro Nishino、Keisuke Takahashi

  DOI：10.3987/com-09-s(s)86

  日期：——

  A methodology feasible for the stereoselective synthesis of clutiolide, a secolabdane diterpene from Clutia abyssinica, was developed based on a remote chelation controlled Ireland-Claisen rearrangement.

  基于远程螯合控制的 Ireland-Claisen 重排，开发了一种可行的立体选择性合成 Clutiolide（一种来自 Clutia abyssinica 的 secolabdane 二萜）的方法。
• Polystyrene-Supported TRIP: A Highly Recyclable Catalyst for Batch and Flow Enantioselective Allylation of Aldehydes
  作者：Lidia Clot-Almenara、Carles Rodríguez-Escrich、Laura Osorio-Planes、Miquel A. Pericàs

  DOI：10.1021/acscatal.6b02621

  日期：2016.11.4

  The widely applicable TRIP phosphoric acid catalyst has been immobilized on polystyrene using a copolymerization-based strategy. The resin (PS-TRIP) has proven to be highly active and enantioselective in the asymmetric allylboration of aldehydes. Moreover, it has shown to be extremely robust, as it can be reused for 18 times, after which it still retained its activity. Lastly, to further prove the

  广泛适用的TRIP磷酸催化剂已使用基于共聚的策略固定在聚苯乙烯上。事实证明，该树脂（PS-TRIP）在醛的不对称烯丙基硼化反应中具有很高的活性和对映选择性。而且，它已经显示出非常强大的功能，因为它可以重复使用18次，之后仍然保持其活动状态。最后，为了进一步证明固定化的好处，已经进行了长达28小时的连续流动实验，其收率和ee很高。
• <i>cis</i>-2,5-Diaminobicyclo[2.2.2]octane, a New Scaffold for Asymmetric Catalysis via Salen−Metal Complexes
  作者：James D. White、Subrata Shaw

  DOI：10.1021/ol2007378

  日期：2011.5.6

  A new C2 symmetric salen scaffold based on cis-2,5-diaminobicyclo[2.2.2]octane has been synthesized that forms complexes with a wide range of metals. The chromium(III) complex is shown to catalyze the hetero-Diels−Alder reaction and the Nozaki−Hiyama−Kishi reaction with high efficiency and excellent stereoselectivity.

  合成了一种新的基于顺式-2,5-二氨基双环[2.2.2]辛烷的C 2对称塞伦骨架，该骨架与多种金属形成配合物。铬（III）络合物显示出以高效率和出色的立体选择性催化杂Diels-Alder反应和Nozaki-Hiyama-Kishi反应。
• Chiral synthesis via organoboranes. 36. Exceptionally enantioselective allylborations of representative heterocyclic aldehydes at -100 .degree.C under salt-free conditions
  作者：Uday S. Racherla、Yi Liao、Herbert C. Brown

  DOI：10.1021/jo00050a045

  日期：1992.11

  Chiral terpenyl-based allylborane reagents (Ter2*BCH2CH=CH2, 1-3) undergo facile condensation with representative heterocyclic aldehydes (HetCHO) at -100-degrees-C (in the absence of Mg2+ salts) and afford the corresponding homoallylic alcohols (HetCH*(OH)CH2CH=CH2,12-19) in enantiomeric purities approaching 100% ee. A new workup procedure involving 8-hydroxyquinoline (8-HQ) has been utilized for the convenient isolation of the product alcohols.