rac-1-allylcyclopent-2-enol | 73057-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-1-allylcyclopent-2-enol
• 英文别名: 1-allyl-2-cyclopenten-1-ol；1-allylcyclopent-2-en-1-ol；1-Prop-2-enylcyclopent-2-en-1-ol
• CAS: 73057-68-8
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: DOVYSRIKJOWLIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  rac-1-allylcyclopent-2-enol 在 sodium tetrahydroborate 、 重铬酸吡啶 、 cerium(III) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-allyl-2-cyclopenten-1-ol
  参考文献：
  名称：

  通过有机锂介导的β-烷氧基氮丙啶向环戊烯基胺的转化，形成氮杂螺环的新途径。

  摘要：

  已开发出一种新的三步合成氮杂螺环化合物的方法，该方法涉及有机锂介导的β-烷氧基氮丙啶转化为取代的环戊烯基胺，进行硼氢化和环化反应。该方法被用于头孢他辛五环体系的构建。[反应：看文字]

  DOI：

  10.1021/ol062073e
• 作为产物：
  描述：

  2-环戊烯酮 、 3-溴丙烯 在 碘 、 magnesium 、 氯化铵 作用下， 以 乙醚 、 四氢呋喃 、 水 为溶剂， 反应 4.42h， 以92%的产率得到rac-1-allylcyclopent-2-enol
  参考文献：
  名称：

  Chemoenzymatic route to various spirocyclic compounds based on enantiomerically enriched tertiary allylic, homoallylic, and homopropargylic alcohols

  摘要：

  A ring closing metathesis (RCM) reaction of dienes and an intramolecular Pauson-Khand (PKR) reaction of enynes derived from tertiary allyl, homoallyl, and homopropargyl alcohol backbones to afford the corresponding spirocyclic dihydrofuran and dihydropyrans and spirocyclic cyclopentenone pyrans, respectively, are described. Cyclopent-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols la-c have been efficiently resolved via enzymatic resolution with high ee (up to 90%) with 44%, 40%, and 43% chemical yields, respectively. Moreover, the cyclohex-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols 3a-c have also been resolved in the same manner with high ee (up to 97%) and in 42%, 45%, and 49% chemical yields. Enantiomerically enriched dienes derived from tertiary homoallyl alcohols yield the corresponding enantiomerically enriched spirocyclic dihydropyran derivatives via RCM with 74% and 78% chemical yields and with 90% and 97% ee, respectively. Moreover, enantiomerically enriched enynes derived from tertiary homoallyl alcohols afford the corresponding enantiomerically enriched cyclopentenone pyrans with spirocyclic motifs via PKR with 80% and 81% chemical yields, respectively, and as single diastereomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.004

文献信息

• π-Allyi lanthanoid ate complex as a new highly 1,2-regioselective allyl transfer agent for α,β-unsaturated carbonyl compounds
  作者：Shin-ichi Fukuzawa、Ken Sato、Tatsuo Fujinami、Shizuyoshi Sakai

  DOI：10.1039/c39900000939

  日期：——

  The π-allyi lanthanoid ate complex (1), which was prepared in situ from tetra-allyltin, the lanthanoid trichloride, and n-butyl-lithium in tetrahydrofuran (THF), reacts smoothly with α,β-unsaturated carbonyl compounds (3)–(11) with a high degree of 1,2-regioselectivity to give 3-hydroxy-1, 5-dienes (12)–(20) in good to excellent yields.

  由四烯丙基，三氯化镧和正丁基锂在四氢呋喃（THF）中原位制备的π-烯丙基镧系元素配合物（1）与α，β-不饱和羰基化合物（3）平稳反应。-（11）具有高度的1,2-区域选择性，可产生3-羟基-1，5-二烯（12）-（20），产率高至优异。
• Optically active tertiary alcohols by biocatalysis
  作者：Devrim Özdemirhan

  DOI：10.1080/00397911.2016.1274032

  日期：2017.4.3

  chemoenzymatic route to optically active aromatic ring-fused cyclic tertiary alcohols (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a has been reported.[9] CAL-A (lipase-A from Candida antarctica) was found the best biocatalyst for 1b, CAL-A cross linked enzyme aggregate (CLEA) for 1a, with ee values of 20 and 45% and the esters 2b and 2a with ee values

  摘要 最初，化学酶法制备光学活性芳香环稠环叔醇 (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S) -(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a 已有报道。[9] CAL-A（来自南极念珠菌的脂肪酶-A）被发现是 1b 的最佳生物催化剂，CAL-A 交联酶聚集体 (CLEA) 是 1a 的 ee 值为 20% 和 45%，酯 2b 和 2a 的 ee 值为 99和 71%。然后，环戊二烯锚定的叔烯丙基 1a'、高烯丙基 1b' 和高炔丙基 1c 醇以高 ee（高达 90%）进行酶促拆分，化学收率分别为 44%、40% 和 43%，环己基 2 -ene 在高 ee（高达 97%）中锚定叔烯丙基 3a、高烯丙基 3b 和高炔丙基 3c 醇，化学产率依次为 42%、45% 和
• [EN] 4-SUBSTITUTED IMIDAZOLE-2-THIONES AND IMIDAZOL-2-ONES AS AGONISTS OF THE ALPHA-2B AND ALPHA-2C ADRENERGIC RECEPTORS<br/>[FR] IMIDAZOLE-2-ONES ET IMIDAZOLE-2-THIONES 4 SUBSTITUES COMME AGONISTES DES ADRENO-RECEPTEURS ALPHA-2B ET ALPHA-2C
  申请人：ALLERGAN INC

  公开号：WO2003099795A1

  公开（公告）日：2003-12-04

  Compounds of Formula (I): where X is S and the variables have the meaning defined in the specification are specific or selective to alpha2B and/or alpha2C adrenergic receptors in preference over alpha2A adrenergic receptors, and as such have no or only minimal cardivascular and/or sedatory activity. These compounds of Formula (I) are useful as medicaments in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha2B adrenergic receptors. Compounds of Formula (I) where X is O also have the advantageous property that they have no or only minimal cardivascular and/or sedatory activity and are useful for treating pain and other conditions with no or only minimal cardivascular and/or sedatory activity.

  式(I)的化合物：其中X为S，变量的含义如规范中定义的那样，对alpha2B和/或alpha2C肾上腺素受体具有特异性或选择性，优先于alpha2A肾上腺素受体，并且因此具有无或仅有极小的心血管和/或镇静活性。这些式(I)的化合物在哺乳动物，包括人类中，作为药物用于治疗对alpha2B肾上腺素受体激动剂治疗有响应的疾病和/或缓解症状是有用的。式(I)的化合物，其中X为O，还具有有利的特性，即它们具有无或仅有极小的心血管和/或镇静活性，并且适用于治疗无或仅有极小的心血管和/或镇静活性的疼痛和其他症状。
• Stereoselective aziridination of cyclic allylic alcohols using chloramine-T
  作者：Susannah C. Coote、Peter O'Brien、Adrian C. Whitwood

  DOI：10.1039/b811137e

  日期：——

  TsNClNa and t-BuSO(2)NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis-diastereoselectivity was observed in the aziridination of 1,3-disubstituted

  已探索了使用两种不同的氯胺盐（4-MeC（6）H（4）SO（2）NClNa，TsNClNa和t-BuSO（2）NClNa，BusNClNa）对一系列环状烯丙基醇进行立体选择性叠氮化。这些反应的立体选择性高度依赖于烯丙基醇和氯胺盐的结构。通常，获得顺式和反式-羟基氮丙啶的混合物，其中主要的非对映异构体是顺式-羟基氮丙啶，而在1，3-二取代的烯丙基醇的叠氮化中观察到完全的顺式-非对映选择性。在每种研究的情况下，与使用TsNClNa进行相同反应所观察到的相比，使用BusNClNa进行叠氮化可以得到更高的顺式-立体选择性。出乎意料的是，将叠氮化条件应用于1-取代的环戊-2-烯-1-醇不会产生氮丙啶。反而，
• 4-(2-Methyl-5,6,7,8-tetrahydro-quinolin-7-ylmethyl)-1,3-dihydro-imidazole-2-thione as specific alpha2B agonist and methods of using the same
  申请人：Heidelbaugh M. Todd

  公开号：US20050075366A1

  公开（公告）日：2005-04-07

  The compound of the formula wherein the * indicates an asymmetric carbon, is specific to alpha 2B adrenergic receptors in preference over alpha 2A and alpha 2C adrenergic receptors, and as such has no or only minimal cardivascular and/or sedatory activity. The compound is useful as medicament in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha 2B adrenergic receptors.

  该化学式的化合物，其中*表示一个不对称碳原子，对α2B肾上腺素受体具有特异性，优先于α2A和α2C肾上腺素受体，因此几乎没有或仅有极小的心血管和/或镇静活性。该化合物可用作哺乳动物，包括人类，治疗对α2B肾上腺素受体激动剂治疗敏感的疾病和/或缓解症状的药物。