3-methyl-2-(trans-1-pentenyl)-2-cyclopenten-1-one | 87506-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-2-(trans-1-pentenyl)-2-cyclopenten-1-one
• 英文别名: (E)-3-methyl-(2-pent-1-enyl)cyclopent-2-enone；3-methyl-2-(trans-1-pentenyl)-2-cyclopentenone；3-methyl-2-[(E)-pent-1-enyl]cyclopent-2-en-1-one
• CAS: 87506-04-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: HSOCLPVBLYBQSN-AATRIKPKSA-N

物化性质

• 沸点：
  264.6±10.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  3-methyl-2-(trans-1-pentenyl)-2-cyclopenten-1-one 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到二氢茉莉酮
  参考文献：
  名称：

  Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

  摘要：

  An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2CL2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.107
• 作为产物：
  描述：

  5-pentylidene-1,3-cyclopentadiene 在 5,10,15,20-tetrakisphenylporphyrin 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-methyl-2-(trans-1-pentenyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

  摘要：

  An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2CL2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.107

文献信息

• Synthesis of<i>cis</i>-Jasmone<i>via</i>the Retroaldol-aldol Condensation of 3-(<i>cis</i>-3-Hexenyl)-2-cyclopentenone in an Autoclave
  作者：Takashi Yoshida、Shojiro Saito

  DOI：10.1246/bcsj.55.3931

  日期：1982.12

  cis-Jasmone was efficiently synthesized from 2-cyclopentenone. The treatment of 2-cyclopentenone with sodium p-toluenesulfinate gave 3-(p-tolylsulfonyl)cyclopentanone in a 92.5% yield. The alkylation of the sulfone, after the protection of the ketone, with cis-1-bromo-3-hexene, followed by desulfonylation with 5% hydrochloric acid in tetrahydrofuran, afforded 3-(cis-3-hexenyl)-2-cyclopentenone in a good yield. The retroaldol-aldol condensation of the cyclopentenone in a stainless steel autoclave in presence of 5% sodium hydroxide yielded cis-jasmone in a 80% yield.

  cis-茉莉酮是通过2-环戊烯酮高效合成的。将2-环戊烯酮与对甲苯磺酸钠反应，获得3-(对甲苯基磺酰)环戊酮，产率为92.5%。在保护酮之后，用cis-1-溴-3-己烯对磺酮进行烷基化，然后用5%的盐酸在四氢呋喃中进行去磺化，得到3-(cis-3-己烯基)-2-环戊烯酮，产率良好。在不锈钢高压釜中，使用5%氢氧化钠对环戊烯酮进行逆醇缩-醇缩缩合反应，产得cis-茉莉酮，产率为80%。
• Ring expansion of succinoin derivatives. New synthetic routes to cyclopentenones
  作者：Eiichi Nakamura、Jun-ichi Shimada、Isao Kuwajima

  DOI：10.1039/c39830000498

  日期：——

  Acid-catalysed ring expansion reactions of cyclobutane derivatives bearing a vicinal substituted-diol group give α-aryl and α-vinyl substituted cyclopentenones in good yields.

  带有邻位取代的二醇基团的环丁烷衍生物的酸催化的扩环反应以良好的产率得到α-芳基和α-乙烯基取代的环戊烯酮。
• NOVEL PROCESS FOR PREPARING SYNTHESIS INTERMEDIATES USING PRODUCTS OF NATURAL ORIGIN AND USE OF THE INTERMEDIATES OBTAINED
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20170327449A1

  公开（公告）日：2017-11-16

  Disclosed is a process for preparing a product of formula I: wherein the reaction is catalyzed both by thiamine or a thiamine salt and by ascorbic acid in a form which is free or salified or an organic acid salt of an alkaline metal, preferably sodium acetate, potassium tartrate, sodium succinate, or a reductone, preferably 2-hydroxypropanedial or 2,3-dihydroxycyclopent-2-ene-1-one in an organic solvent.

  公开了一种制备式I产品的过程：其中反应既由硫胺素或硫胺素盐催化，又由抗坏血酸以自由或盐化形式或碱金属有机酸盐，优选为乙酸钠、酒石酸钾、琥珀酸钠或还原酮，优选为2-羟基丙二醛或2,3-二羟基环戊-2-烯-1-酮，在有机溶剂中。
• Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods
  作者：Junichi Shimada、Koichi Hashimoto、Byeang Hyean Kim、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1021/ja00318a035

  日期：1984.3
• NAKAMURA, EIICHI;SHIMADA, JUN-ICHI;KUWAJIMA, ISAO, J. CHEM. SOC. CHEM. COMMUN., 1983, N 9, 498-499
  作者：NAKAMURA, EIICHI、SHIMADA, JUN-ICHI、KUWAJIMA, ISAO

  DOI：——

  日期：——