2-isopropylcyclobutanone | 27608-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-isopropylcyclobutanone
• 英文别名: 2-Isopropyl-cyclobutanon；2-(Propan-2-yl)cyclobutan-1-one；2-propan-2-ylcyclobutan-1-one
• CAS: 27608-63-5
• 化学式: C₇H₁₂O
• mdl: MFCD24688910
• 分子量: 112.172
• InChiKey: SHZQRYVAUCNNAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-isopropylcyclobutanone 在 palladium dihydroxide 盐酸 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 120.0h， 生成 (1S,2S)-1-amino-2-isopropylcyclobutanecarboxylic acid hydrochloride
  参考文献：
  名称：

  First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones

  摘要：

  An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00073-9
• 作为产物：
  描述：

  2-异丙基环丁酮 在 氢气 、 铂 作用下， 生成 2-isopropylcyclobutanone
  参考文献：
  名称：

  Lebedew, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 831

  摘要：

  DOI：

文献信息

• Pyrazole glucokinase activators
  申请人：Berthel Steven Joseph

  公开号：US20080021032A1

  公开（公告）日：2008-01-24

  Disclosed herein are pyrazole glucokinase activators of the formula (I) useful for the treatment of metabolic diseases and disorders, preferably diabetes mellitus.

  本文披露了一种式(I)的吡唑葡萄糖激酶激活剂，用于治疗代谢性疾病和紊乱，最好是糖尿病。
• A Novel Route to Geminal Dibromocyclobutanes:  Syntheses of 2-Substituted Cyclobutanone Acetals and Their Reaction with Boron Tribromide
  作者：Tore Nordvik、Udo H. Brinker

  DOI：10.1021/jo035295o

  日期：2003.11.1

  Nine 2-substituted cyclobutanone acetals, in addition to the parent cyclobutanone acetal, were synthesized from their corresponding cyclobutanones and subsequently treated with boron tribromide. The substituents were either alkyl chains or a phenyl and a benzyl group, respectively. The major compounds obtained in these reactions were, in most cases, the geminal dibromocyclobutanes which were obtained

  除了母体环丁酮缩醛以外，还从它们相应的环丁酮合成了九个2-取代的环丁酮缩醛，随后用三溴化硼处理。取代基分别为烷基链或苯基和苄基。在大多数情况下，这些反应中获得的主要化合物是双溴双环丁烷，其收率在50％到73％之间。过量2倍的BBr3和在-78摄氏度下3小时的反应时间可提供最佳收率。在四种情况下，根本没有观察到二溴化物的形成，并且环丁酮缩醛被水解为相应的环丁酮。这可能是由于过渡态中乙缩醛和BBr3的位阻增加所致。
• Organic synthesis using a hypervalent iodine reagent: unexpected and novel domino reaction leading to spiro cyclohexadienone lactones
  作者：Hiromichi Fujioka、Hideyuki Komatsu、Taeko Nakamura、Akihito Miyoshi、Kayoko Hata、Jnashuara Ganesh、Kenichi Murai、Yasuyuki Kita

  DOI：10.1039/b925687c

  日期：——

  The reaction of 1-(p-hydroxyaryl)cyclobutanols and phenyl iodide(III) diacetate in hexafluoroisopropanol and water produced spiro cyclohexadienone lactones via a domino reaction.

  在六氟异丙醇和水反应条件下，1-(对羟基芳基)环丁醇与苯碘(III)二乙酸酯通过联锁反应生成螺环己二烯酮内酯。
• Metalloprotease inhibitors containing a heterocyclic moiety
  申请人：Gege Christian

  公开号：US20080221091A1

  公开（公告）日：2008-09-11

  The present invention relates generally to pharmaceutical agents containing a heterocyclic moiety, and in particular, to heterocyclic metalloprotease inhibiting compounds. More particularly, the present invention provides a new class of heterocyclic MMP-13 inhibiting compounds with a modified benzoxazine moiety, that exhibit an increased potency and selectivity in relation to currently known MMP-13 inhibitors.

  本发明涉及一般含有杂环基团的药物制剂，特别是杂环金属蛋白酶抑制化合物。更具体地说，本发明提供了一类新型的含有改性苯并噁嗪基团的杂环MMP-13抑制化合物，其在与目前已知的MMP-13抑制剂相比具有增强的效力和选择性。
• Synthetic Studies toward Halichlorine: Complex Azaspirocycle Formation with Use of an NBS-Promoted Semipinacol Reaction
  作者：Paul B. Hurley、Gregory R. Dake

  DOI：10.1021/jo800336k

  日期：2008.6.1

  The investigations of a synthetic route incorporating a NBS-promoted semipinacol rearrangement to the 6-azaspiro[4.5]decane fragment within halichlorine (1) are presented. A convergent approach was pursued, utilizing two chiral, enantiomerically enriched building blocks, 2-trimethylstannyl piperidene 10 and substituted cyclobutanone 19. Noteworthy synthetic operations in this study include the following:

  提出了一种合成途径的研究，该途径结合了NBS促进的半频哪醇重排至盐酸中的6-氮杂螺[4.5]癸烷片段（1）。寻求一种收敛的方法，利用两个手性，对映体富集的结构单元，2-三甲基锡烷基哌啶烯10和取代的环丁酮19。这项研究中值得注意的合成操作包括：（a）NBS促进的非对映选择性很高的半频哪醇反应，该反应在酮25中建立了四个立体生成中心，以及（b）使用N - p-甲苯磺酰基-2-碘-2-哌啶烯作为碱性有机金属试剂的前体，这对片段10和19的成功偶联至关重要。